id sid tid token lemma pos c247dr2924g 1 1 this this DET c247dr2924g 1 2 dissertation dissertation NOUN c247dr2924g 1 3 will will AUX c247dr2924g 1 4 cover cover VERB c247dr2924g 1 5 cyclopropane cyclopropane NOUN c247dr2924g 1 6 methodology methodology NOUN c247dr2924g 1 7 for for ADP c247dr2924g 1 8 the the DET c247dr2924g 1 9 synthesis synthesis NOUN c247dr2924g 1 10 of of ADP c247dr2924g 1 11 1,2,3 1,2,3 PROPN c247dr2924g 1 12 - - PUNCT c247dr2924g 1 13 trisubstituted trisubstitute VERB c247dr2924g 1 14 cyclopropanes cyclopropane NOUN c247dr2924g 1 15 . . PUNCT c247dr2924g 2 1 we we PRON c247dr2924g 2 2 envisioned envision VERB c247dr2924g 2 3 building build VERB c247dr2924g 2 4 a a DET c247dr2924g 2 5 cyclopropane cyclopropane NOUN c247dr2924g 2 6 precursor precursor NOUN c247dr2924g 2 7 with with ADP c247dr2924g 2 8 two two NUM c247dr2924g 2 9 main main ADJ c247dr2924g 2 10 features feature NOUN c247dr2924g 2 11 . . PUNCT c247dr2924g 3 1 the the DET c247dr2924g 3 2 first first ADJ c247dr2924g 3 3 feature feature NOUN c247dr2924g 3 4 was be AUX c247dr2924g 3 5 to to PART c247dr2924g 3 6 use use VERB c247dr2924g 3 7 the the DET c247dr2924g 3 8 known know VERB c247dr2924g 3 9 equilibrium equilibrium NOUN c247dr2924g 3 10 between between ADP c247dr2924g 3 11 the the DET c247dr2924g 3 12 homoallylic homoallylic ADJ c247dr2924g 3 13 cation cation NOUN c247dr2924g 3 14 , , PUNCT c247dr2924g 3 15 the the DET c247dr2924g 3 16 cyclobutane cyclobutane ADJ c247dr2924g 3 17 cation cation NOUN c247dr2924g 3 18 , , PUNCT c247dr2924g 3 19 and and CCONJ c247dr2924g 3 20 the the DET c247dr2924g 3 21 cyclopropyl cyclopropyl PROPN c247dr2924g 3 22 carbinyl carbinyl PROPN c247dr2924g 3 23 cation cation NOUN c247dr2924g 3 24 . . PUNCT c247dr2924g 4 1 we we PRON c247dr2924g 4 2 incorporated incorporate VERB c247dr2924g 4 3 this this DET c247dr2924g 4 4 feature feature NOUN c247dr2924g 4 5 by by ADP c247dr2924g 4 6 having have VERB c247dr2924g 4 7 a a DET c247dr2924g 4 8 homoallylic homoallylic NOUN c247dr2924g 4 9 group group NOUN c247dr2924g 4 10 ( ( PUNCT c247dr2924g 4 11 x x SYM c247dr2924g 4 12 ) ) PUNCT c247dr2924g 4 13 displaced displace VERB c247dr2924g 4 14 with with ADP c247dr2924g 4 15 allylsilane allylsilane PROPN c247dr2924g 4 16 forming form VERB c247dr2924g 4 17 the the DET c247dr2924g 4 18 cyclopropyl cyclopropyl PROPN c247dr2924g 4 19 carbinyl carbinyl PROPN c247dr2924g 4 20 cation cation NOUN c247dr2924g 4 21 . . PUNCT c247dr2924g 5 1 this this DET c247dr2924g 5 2 cation cation NOUN c247dr2924g 5 3 would would AUX c247dr2924g 5 4 then then ADV c247dr2924g 5 5 begin begin VERB c247dr2924g 5 6 to to PART c247dr2924g 5 7 equilibrate equilibrate VERB c247dr2924g 5 8 . . PUNCT c247dr2924g 6 1 however however ADV c247dr2924g 6 2 , , PUNCT c247dr2924g 6 3 the the DET c247dr2924g 6 4 second second ADJ c247dr2924g 6 5 feature feature NOUN c247dr2924g 6 6 was be AUX c247dr2924g 6 7 to to PART c247dr2924g 6 8 include include VERB c247dr2924g 6 9 a a DET c247dr2924g 6 10 silyl silyl NOUN c247dr2924g 6 11 group group NOUN c247dr2924g 6 12 ? ? PUNCT c247dr2924g 7 1 to to ADP c247dr2924g 7 2 the the DET c247dr2924g 7 3 olefin olefin NOUN c247dr2924g 7 4 and and CCONJ c247dr2924g 7 5 in in ADP c247dr2924g 7 6 a a DET c247dr2924g 7 7 position position NOUN c247dr2924g 7 8 to to PART c247dr2924g 7 9 stabilize stabilize VERB c247dr2924g 7 10 the the DET c247dr2924g 7 11 forming form VERB c247dr2924g 7 12 cyclopropyl cyclopropyl PROPN c247dr2924g 7 13 carbinyl carbinyl PROPN c247dr2924g 7 14 cation cation NOUN c247dr2924g 7 15 with with ADP c247dr2924g 7 16 the the DET c247dr2924g 7 17 ? ? PROPN c247dr2924g 7 18 -silicon -silicon ADJ c247dr2924g 7 19 effect effect NOUN c247dr2924g 7 20 and and CCONJ c247dr2924g 7 21 therefore therefore ADV c247dr2924g 7 22 drive drive VERB c247dr2924g 7 23 the the DET c247dr2924g 7 24 equilibrium equilibrium NOUN c247dr2924g 7 25 toward toward ADP c247dr2924g 7 26 the the DET c247dr2924g 7 27 cyclopropane cyclopropane NOUN c247dr2924g 7 28 . . PUNCT c247dr2924g 8 1 the the DET c247dr2924g 8 2 silicon silicon NOUN c247dr2924g 8 3 was be AUX c247dr2924g 8 4 necessary necessary ADJ c247dr2924g 8 5 to to PART c247dr2924g 8 6 make make VERB c247dr2924g 8 7 sure sure ADJ c247dr2924g 8 8 that that SCONJ c247dr2924g 8 9 ring ring NOUN c247dr2924g 8 10 fragmentation fragmentation NOUN c247dr2924g 8 11 and and CCONJ c247dr2924g 8 12 subsequent subsequent ADJ c247dr2924g 8 13 1,2 1,2 NOUN c247dr2924g 8 14 - - PUNCT c247dr2924g 8 15 elimination elimination NOUN c247dr2924g 8 16 did do AUX c247dr2924g 8 17 not not PART c247dr2924g 8 18 occur occur VERB c247dr2924g 8 19 . . PUNCT c247dr2924g 9 1 also also ADV c247dr2924g 9 2 , , PUNCT c247dr2924g 9 3 the the DET c247dr2924g 9 4 facile facile NOUN c247dr2924g 9 5 elimination elimination NOUN c247dr2924g 9 6 of of ADP c247dr2924g 9 7 silicon silicon NOUN c247dr2924g 9 8 allowed allow VERB c247dr2924g 9 9 us we PRON c247dr2924g 9 10 to to PART c247dr2924g 9 11 trap trap VERB c247dr2924g 9 12 the the DET c247dr2924g 9 13 cyclopropane cyclopropane NOUN c247dr2924g 9 14 , , PUNCT c247dr2924g 9 15 which which PRON c247dr2924g 9 16 resulted result VERB c247dr2924g 9 17 in in ADP c247dr2924g 9 18 a a DET c247dr2924g 9 19 terminal terminal ADJ c247dr2924g 9 20 olefin olefin NOUN c247dr2924g 9 21 which which PRON c247dr2924g 9 22 can can AUX c247dr2924g 9 23 be be AUX c247dr2924g 9 24 elaborated elaborate VERB c247dr2924g 9 25 further far ADV c247dr2924g 9 26 . . PUNCT c247dr2924g 10 1 the the DET c247dr2924g 10 2 ' ' PUNCT c247dr2924g 10 3 state state NOUN c247dr2924g 10 4 of of ADP c247dr2924g 10 5 the the DET c247dr2924g 10 6 art art NOUN c247dr2924g 10 7 ' ' PUNCT c247dr2924g 10 8 at at ADP c247dr2924g 10 9 the the DET c247dr2924g 10 10 time time NOUN c247dr2924g 10 11 of of ADP c247dr2924g 10 12 my my PRON c247dr2924g 10 13 arrival arrival NOUN c247dr2924g 10 14 entailed entail VERB c247dr2924g 10 15 building build VERB c247dr2924g 10 16 the the DET c247dr2924g 10 17 cyclopropane cyclopropane NOUN c247dr2924g 10 18 precursor precursor NOUN c247dr2924g 10 19 with with ADP c247dr2924g 10 20 a a DET c247dr2924g 10 21 boron boron NOUN c247dr2924g 10 22 acetylide acetylide NOUN c247dr2924g 10 23 opening opening NOUN c247dr2924g 10 24 of of ADP c247dr2924g 10 25 mono mono PROPN c247dr2924g 10 26 - - PUNCT c247dr2924g 10 27 substituted substitute VERB c247dr2924g 10 28 epoxides epoxide NOUN c247dr2924g 10 29 . . PUNCT c247dr2924g 11 1 this this DET c247dr2924g 11 2 methodology methodology NOUN c247dr2924g 11 3 allowed allow VERB c247dr2924g 11 4 us we PRON c247dr2924g 11 5 to to PART c247dr2924g 11 6 prove prove VERB c247dr2924g 11 7 our our PRON c247dr2924g 11 8 concept concept NOUN c247dr2924g 11 9 , , PUNCT c247dr2924g 11 10 but but CCONJ c247dr2924g 11 11 was be AUX c247dr2924g 11 12 limited limit VERB c247dr2924g 11 13 toward toward ADP c247dr2924g 11 14 the the DET c247dr2924g 11 15 synthesis synthesis NOUN c247dr2924g 11 16 of of ADP c247dr2924g 11 17 trisubstituted trisubstitute VERB c247dr2924g 11 18 cyclopropanes cyclopropane NOUN c247dr2924g 11 19 . . PUNCT c247dr2924g 12 1 therefore therefore ADV c247dr2924g 12 2 we we PRON c247dr2924g 12 3 proposed propose VERB c247dr2924g 12 4 a a DET c247dr2924g 12 5 method method NOUN c247dr2924g 12 6 highlighted highlight VERB c247dr2924g 12 7 by by ADP c247dr2924g 12 8 the the DET c247dr2924g 12 9 formation formation NOUN c247dr2924g 12 10 of of ADP c247dr2924g 12 11 the the DET c247dr2924g 12 12 cyclopropane cyclopropane NOUN c247dr2924g 12 13 precursor precursor NOUN c247dr2924g 12 14 using use VERB c247dr2924g 12 15 rcm rcm NOUN c247dr2924g 12 16 chemistry chemistry NOUN c247dr2924g 12 17 . . PUNCT c247dr2924g 13 1 the the DET c247dr2924g 13 2 goal goal NOUN c247dr2924g 13 3 was be AUX c247dr2924g 13 4 to to PART c247dr2924g 13 5 investigate investigate VERB c247dr2924g 13 6 the the DET c247dr2924g 13 7 closure closure NOUN c247dr2924g 13 8 of of ADP c247dr2924g 13 9 substituted substituted ADJ c247dr2924g 13 10 cyclopropane cyclopropane NOUN c247dr2924g 13 11 precursors precursor NOUN c247dr2924g 13 12 and and CCONJ c247dr2924g 13 13 determine determine VERB c247dr2924g 13 14 the the DET c247dr2924g 13 15 stereochemical stereochemical ADJ c247dr2924g 13 16 course course NOUN c247dr2924g 13 17 of of ADP c247dr2924g 13 18 the the DET c247dr2924g 13 19 reaction reaction NOUN c247dr2924g 13 20 . . PUNCT c247dr2924g 14 1 the the DET c247dr2924g 14 2 new new ADJ c247dr2924g 14 3 method method NOUN c247dr2924g 14 4 allowed allow VERB c247dr2924g 14 5 us we PRON c247dr2924g 14 6 to to PART c247dr2924g 14 7 start start VERB c247dr2924g 14 8 from from ADP c247dr2924g 14 9 a a DET c247dr2924g 14 10 substituted substitute VERB c247dr2924g 14 11 homoallylic homoallylic NOUN c247dr2924g 14 12 alcohol alcohol NOUN c247dr2924g 14 13 and and CCONJ c247dr2924g 14 14 in in ADP c247dr2924g 14 15 three three NUM c247dr2924g 14 16 transformations transformation NOUN c247dr2924g 14 17 yield yield VERB c247dr2924g 14 18 the the DET c247dr2924g 14 19 desired desire VERB c247dr2924g 14 20 precursor precursor NOUN c247dr2924g 14 21 . . PUNCT c247dr2924g 15 1 there there PRON c247dr2924g 15 2 are be VERB c247dr2924g 15 3 many many ADJ c247dr2924g 15 4 methods method NOUN c247dr2924g 15 5 known know VERB c247dr2924g 15 6 for for ADP c247dr2924g 15 7 the the DET c247dr2924g 15 8 preparation preparation NOUN c247dr2924g 15 9 of of ADP c247dr2924g 15 10 suitable suitable ADJ c247dr2924g 15 11 homoallylic homoallylic ADJ c247dr2924g 15 12 alcohols alcohol NOUN c247dr2924g 15 13 . . PUNCT c247dr2924g 16 1 however however ADV c247dr2924g 16 2 , , PUNCT c247dr2924g 16 3 for for ADP c247dr2924g 16 4 this this DET c247dr2924g 16 5 summary summary NOUN c247dr2924g 16 6 i i PRON c247dr2924g 16 7 will will AUX c247dr2924g 16 8 only only ADV c247dr2924g 16 9 highlight highlight VERB c247dr2924g 16 10 the the DET c247dr2924g 16 11 results result NOUN c247dr2924g 16 12 obtained obtain VERB c247dr2924g 16 13 from from ADP c247dr2924g 16 14 homoallylic homoallylic ADJ c247dr2924g 16 15 alcohols alcohol NOUN c247dr2924g 16 16 derived derive VERB c247dr2924g 16 17 from from ADP c247dr2924g 16 18 an an DET c247dr2924g 16 19 indium indium NOUN c247dr2924g 16 20 mediated mediate VERB c247dr2924g 16 21 crotylation crotylation NOUN c247dr2924g 16 22 of of ADP c247dr2924g 16 23 hydrocinnamaldehyde hydrocinnamaldehyde PROPN c247dr2924g 16 24 . . PUNCT c247dr2924g 17 1 the the DET c247dr2924g 17 2 indium indium PROPN c247dr2924g 17 3 mediated mediate VERB c247dr2924g 17 4 crotylation crotylation NOUN c247dr2924g 17 5 resulted result VERB c247dr2924g 17 6 in in ADP c247dr2924g 17 7 a a DET c247dr2924g 17 8 3:1 3:1 NUM c247dr2924g 17 9 mixture mixture NOUN c247dr2924g 17 10 of of ADP c247dr2924g 17 11 anti anti ADJ c247dr2924g 17 12 : : PUNCT c247dr2924g 17 13 syn syn ADJ c247dr2924g 17 14 diastereomers diastereomer NOUN c247dr2924g 17 15 . . PUNCT c247dr2924g 18 1 the the DET c247dr2924g 18 2 predominance predominance NOUN c247dr2924g 18 3 of of ADP c247dr2924g 18 4 anti anti PROPN c247dr2924g 18 5 is be AUX c247dr2924g 18 6 due due ADJ c247dr2924g 18 7 to to ADP c247dr2924g 18 8 a a DET c247dr2924g 18 9 closed close VERB c247dr2924g 18 10 six six NUM c247dr2924g 18 11 membered membered ADJ c247dr2924g 18 12 transition transition NOUN c247dr2924g 18 13 state state NOUN c247dr2924g 18 14 where where SCONJ c247dr2924g 18 15 the the DET c247dr2924g 18 16 crotyl crotyl PROPN c247dr2924g 18 17 indium indium PROPN c247dr2924g 18 18 species species PROPN c247dr2924g 18 19 coordinates coordinate VERB c247dr2924g 18 20 the the DET c247dr2924g 18 21 aldehyde aldehyde NOUN c247dr2924g 18 22 and and CCONJ c247dr2924g 18 23 delivers deliver VERB c247dr2924g 18 24 the the DET c247dr2924g 18 25 crotyl crotyl NOUN c247dr2924g 18 26 group group NOUN c247dr2924g 18 27 when when SCONJ c247dr2924g 18 28 the the DET c247dr2924g 18 29 ethyl ethyl PROPN c247dr2924g 18 30 ester ester PROPN c247dr2924g 18 31 and and CCONJ c247dr2924g 18 32 the the DET c247dr2924g 18 33 r r NOUN c247dr2924g 18 34 group group NOUN c247dr2924g 18 35 on on ADP c247dr2924g 18 36 the the DET c247dr2924g 18 37 aldehyde aldehyde NOUN c247dr2924g 18 38 are be AUX c247dr2924g 18 39 suedo suedo PROPN c247dr2924g 18 40 equatorial equatorial NOUN c247dr2924g 18 41 in in ADP c247dr2924g 18 42 relationship relationship NOUN c247dr2924g 18 43 . . PUNCT c247dr2924g 19 1 the the DET c247dr2924g 19 2 diastereomers diastereomer NOUN c247dr2924g 19 3 were be AUX c247dr2924g 19 4 separated separate VERB c247dr2924g 19 5 by by ADP c247dr2924g 19 6 flash flash NOUN c247dr2924g 19 7 column column NOUN c247dr2924g 19 8 chromatography chromatography NOUN c247dr2924g 19 9 . . PUNCT c247dr2924g 20 1 then then ADV c247dr2924g 20 2 , , PUNCT c247dr2924g 20 3 each each PRON c247dr2924g 20 4 was be AUX c247dr2924g 20 5 taken take VERB c247dr2924g 20 6 on on ADP c247dr2924g 20 7 independently independently ADV c247dr2924g 20 8 to to PART c247dr2924g 20 9 yield yield VERB c247dr2924g 20 10 a a DET c247dr2924g 20 11 single single ADJ c247dr2924g 20 12 1,2,3 1,2,3 NUM c247dr2924g 20 13 - - PUNCT c247dr2924g 20 14 tribubstitued tribubstitue VERB c247dr2924g 20 15 cyclopropane cyclopropane NOUN c247dr2924g 20 16 . . PUNCT c247dr2924g 21 1 the the DET c247dr2924g 21 2 homoallylic homoallylic ADJ c247dr2924g 21 3 alcohol alcohol NOUN c247dr2924g 21 4 was be AUX c247dr2924g 21 5 protected protect VERB c247dr2924g 21 6 with with ADP c247dr2924g 21 7 allylchlorodimethylsilane allylchlorodimethylsilane NOUN c247dr2924g 21 8 followed follow VERB c247dr2924g 21 9 by by ADP c247dr2924g 21 10 closure closure NOUN c247dr2924g 21 11 with with ADP c247dr2924g 21 12 grubbs grubb NOUN c247dr2924g 21 13 ' ' PART c247dr2924g 21 14 ruthenium ruthenium NOUN c247dr2924g 21 15 catalyst catalyst NOUN c247dr2924g 21 16 to to PART c247dr2924g 21 17 afford afford VERB c247dr2924g 21 18 the the DET c247dr2924g 21 19 silyloxycycloheptene silyloxycycloheptene PROPN c247dr2924g 21 20 . . PUNCT c247dr2924g 22 1 the the DET c247dr2924g 22 2 seven seven NUM c247dr2924g 22 3 - - PUNCT c247dr2924g 22 4 membered membered ADJ c247dr2924g 22 5 ring ring NOUN c247dr2924g 22 6 was be AUX c247dr2924g 22 7 opened open VERB c247dr2924g 22 8 with with ADP c247dr2924g 22 9 hf'¢pyridine hf'¢pyridine NUM c247dr2924g 22 10 to to PART c247dr2924g 22 11 give give VERB c247dr2924g 22 12 the the DET c247dr2924g 22 13 desired desire VERB c247dr2924g 22 14 cyclopropane cyclopropane NOUN c247dr2924g 22 15 precursor precursor NOUN c247dr2924g 22 16 bearing bear VERB c247dr2924g 22 17 a a DET c247dr2924g 22 18 fluorosilane fluorosilane NOUN c247dr2924g 22 19 ? ? PUNCT c247dr2924g 23 1 to to ADP c247dr2924g 23 2 the the DET c247dr2924g 23 3 olefin olefin NOUN c247dr2924g 23 4 and and CCONJ c247dr2924g 23 5 a a DET c247dr2924g 23 6 homoallylic homoallylic ADJ c247dr2924g 23 7 alcohol alcohol NOUN c247dr2924g 23 8 ready ready ADJ c247dr2924g 23 9 for for ADP c247dr2924g 23 10 activation activation NOUN c247dr2924g 23 11 . . PUNCT c247dr2924g 24 1 activation activation NOUN c247dr2924g 24 2 was be AUX c247dr2924g 24 3 accomplished accomplish VERB c247dr2924g 24 4 with with ADP c247dr2924g 24 5 triflic triflic ADJ c247dr2924g 24 6 anhydride anhydride NOUN c247dr2924g 24 7 and and CCONJ c247dr2924g 24 8 2,6 2,6 NOUN c247dr2924g 24 9 - - PUNCT c247dr2924g 24 10 lutidine lutidine NOUN c247dr2924g 24 11 in in ADP c247dr2924g 24 12 methylene methylene NOUN c247dr2924g 24 13 chloride chloride PROPN c247dr2924g 24 14 and and CCONJ c247dr2924g 24 15 afforded afford VERB c247dr2924g 24 16 a a DET c247dr2924g 24 17 single single ADJ c247dr2924g 24 18 1,2,3 1,2,3 PROPN c247dr2924g 24 19 - - PUNCT c247dr2924g 24 20 trisubstituted trisubstitute VERB c247dr2924g 24 21 cyclopropane cyclopropane NOUN c247dr2924g 24 22 from from ADP c247dr2924g 24 23 the the DET c247dr2924g 24 24 displacement displacement NOUN c247dr2924g 24 25 of of ADP c247dr2924g 24 26 triflate triflate ADJ c247dr2924g 24 27 and and CCONJ c247dr2924g 24 28 subsequent subsequent ADJ c247dr2924g 24 29 elimination elimination NOUN c247dr2924g 24 30 of of ADP c247dr2924g 24 31 the the DET c247dr2924g 24 32 fluorosilane fluorosilane NOUN c247dr2924g 24 33 . . PUNCT c247dr2924g 25 1 after after SCONJ c247dr2924g 25 2 both both DET c247dr2924g 25 3 diastereomers diastereomer NOUN c247dr2924g 25 4 were be AUX c247dr2924g 25 5 taken take VERB c247dr2924g 25 6 through through ADP c247dr2924g 25 7 the the DET c247dr2924g 25 8 sequence sequence NOUN c247dr2924g 25 9 we we PRON c247dr2924g 25 10 postulated postulate VERB c247dr2924g 25 11 the the DET c247dr2924g 25 12 transition transition NOUN c247dr2924g 25 13 state state NOUN c247dr2924g 25 14 structure structure NOUN c247dr2924g 25 15 that that PRON c247dr2924g 25 16 would would AUX c247dr2924g 25 17 result result VERB c247dr2924g 25 18 in in ADP c247dr2924g 25 19 the the DET c247dr2924g 25 20 formation formation NOUN c247dr2924g 25 21 of of ADP c247dr2924g 25 22 the the DET c247dr2924g 25 23 1,2,3 1,2,3 NUM c247dr2924g 25 24 - - PUNCT c247dr2924g 25 25 cyclopropane cyclopropane NOUN c247dr2924g 25 26 that that PRON c247dr2924g 25 27 resulted result VERB c247dr2924g 25 28 . . PUNCT c247dr2924g 26 1 we we PRON c247dr2924g 26 2 determined determine VERB c247dr2924g 26 3 the the DET c247dr2924g 26 4 relative relative ADJ c247dr2924g 26 5 cyclopropane cyclopropane NOUN c247dr2924g 26 6 stereochemistry stereochemistry NOUN c247dr2924g 26 7 after after ADP c247dr2924g 26 8 several several ADJ c247dr2924g 26 9 1h 1h NOUN c247dr2924g 26 10 - - PUNCT c247dr2924g 26 11 nmr nmr NOUN c247dr2924g 26 12 decoupling decouple VERB c247dr2924g 26 13 experiments experiment NOUN c247dr2924g 26 14 . . PUNCT c247dr2924g 27 1 we we PRON c247dr2924g 27 2 concluded conclude VERB c247dr2924g 27 3 that that SCONJ c247dr2924g 27 4 the the DET c247dr2924g 27 5 reaction reaction NOUN c247dr2924g 27 6 was be AUX c247dr2924g 27 7 an an DET c247dr2924g 27 8 sn2 sn2 PROPN c247dr2924g 27 9 displacement displacement NOUN c247dr2924g 27 10 and and CCONJ c247dr2924g 27 11 that that SCONJ c247dr2924g 27 12 the the DET c247dr2924g 27 13 steric steric ADJ c247dr2924g 27 14 environment environment NOUN c247dr2924g 27 15 controls control VERB c247dr2924g 27 16 the the DET c247dr2924g 27 17 resulting result VERB c247dr2924g 27 18 stereochemistry stereochemistry NOUN c247dr2924g 27 19 . . PUNCT c247dr2924g 28 1 once once SCONJ c247dr2924g 28 2 we we PRON c247dr2924g 28 3 limit limit VERB c247dr2924g 28 4 the the DET c247dr2924g 28 5 discussion discussion NOUN c247dr2924g 28 6 to to ADP c247dr2924g 28 7 an an DET c247dr2924g 28 8 sn2 sn2 PROPN c247dr2924g 28 9 reaction reaction NOUN c247dr2924g 28 10 we we PRON c247dr2924g 28 11 find find VERB c247dr2924g 28 12 there there PRON c247dr2924g 28 13 are be VERB c247dr2924g 28 14 only only ADV c247dr2924g 28 15 two two NUM c247dr2924g 28 16 possible possible ADJ c247dr2924g 28 17 transition transition NOUN c247dr2924g 28 18 states state NOUN c247dr2924g 28 19 that that PRON c247dr2924g 28 20 allow allow VERB c247dr2924g 28 21 for for ADP c247dr2924g 28 22 the the DET c247dr2924g 28 23 anti anti ADJ c247dr2924g 28 24 - - ADJ c247dr2924g 28 25 bonding bonding ADJ c247dr2924g 28 26 orbital orbital ADJ c247dr2924g 28 27 of of ADP c247dr2924g 28 28 the the DET c247dr2924g 28 29 carbon carbon NOUN c247dr2924g 28 30 - - PUNCT c247dr2924g 28 31 triflate triflate ADJ c247dr2924g 28 32 bond bond NOUN c247dr2924g 28 33 to to PART c247dr2924g 28 34 overlap overlap VERB c247dr2924g 28 35 with with ADP c247dr2924g 28 36 the the PRON c247dr2924g 28 37 ? ? PUNCT c247dr2924g 28 38 bond bond NOUN c247dr2924g 28 39 of of ADP c247dr2924g 28 40 the the DET c247dr2924g 28 41 olefin olefin NOUN c247dr2924g 28 42 . . PUNCT c247dr2924g 29 1 the the DET c247dr2924g 29 2 allylsilane allylsilane PROPN c247dr2924g 29 3 can can AUX c247dr2924g 29 4 be be AUX c247dr2924g 29 5 either either CCONJ c247dr2924g 29 6 on on ADP c247dr2924g 29 7 the the DET c247dr2924g 29 8 same same ADJ c247dr2924g 29 9 side side NOUN c247dr2924g 29 10 as as ADP c247dr2924g 29 11 or or CCONJ c247dr2924g 29 12 oppose oppose VERB c247dr2924g 29 13 the the DET c247dr2924g 29 14 ethyl ethyl PROPN c247dr2924g 29 15 ester ester PROPN c247dr2924g 29 16 . . PUNCT c247dr2924g 30 1 we we PRON c247dr2924g 30 2 found find VERB c247dr2924g 30 3 that that SCONJ c247dr2924g 30 4 a a DET c247dr2924g 30 5 classic classic ADJ c247dr2924g 30 6 a a DET c247dr2924g 30 7 - - PUNCT c247dr2924g 30 8 strain strain NOUN c247dr2924g 30 9 argument argument NOUN c247dr2924g 30 10 can can AUX c247dr2924g 30 11 be be AUX c247dr2924g 30 12 used use VERB c247dr2924g 30 13 to to PART c247dr2924g 30 14 determine determine VERB c247dr2924g 30 15 what what PRON c247dr2924g 30 16 transition transition NOUN c247dr2924g 30 17 state state NOUN c247dr2924g 30 18 is be AUX c247dr2924g 30 19 preferred prefer VERB c247dr2924g 30 20 . . PUNCT c247dr2924g 31 1 therefore therefore ADV c247dr2924g 31 2 the the DET c247dr2924g 31 3 allylsilane allylsilane PROPN c247dr2924g 31 4 and and CCONJ c247dr2924g 31 5 the the DET c247dr2924g 31 6 ethylester ethylester NOUN c247dr2924g 31 7 will will AUX c247dr2924g 31 8 oppose oppose VERB c247dr2924g 31 9 each each DET c247dr2924g 31 10 other other ADJ c247dr2924g 31 11 , , PUNCT c247dr2924g 31 12 or or CCONJ c247dr2924g 31 13 the the DET c247dr2924g 31 14 hydrogen hydrogen NOUN c247dr2924g 31 15 ? ? PUNCT c247dr2924g 32 1 to to ADP c247dr2924g 32 2 the the DET c247dr2924g 32 3 carbonyl carbonyl NOUN c247dr2924g 32 4 prefers prefer NOUN c247dr2924g 32 5 to to PART c247dr2924g 32 6 eclipse eclipse VERB c247dr2924g 32 7 the the DET c247dr2924g 32 8 olefin olefin NOUN c247dr2924g 32 9 ( ( PUNCT c247dr2924g 32 10 a a DET c247dr2924g 32 11 - - PUNCT c247dr2924g 32 12 strain strain NOUN c247dr2924g 32 13 ) ) PUNCT c247dr2924g 32 14 . . PUNCT c247dr2924g 33 1 the the DET c247dr2924g 33 2 transition transition NOUN c247dr2924g 33 3 states state NOUN c247dr2924g 33 4 shown show VERB c247dr2924g 33 5 lead lead NOUN c247dr2924g 33 6 to to ADP c247dr2924g 33 7 the the DET c247dr2924g 33 8 cyclopropane cyclopropane NOUN c247dr2924g 33 9 formed form VERB c247dr2924g 33 10 . . PUNCT c247dr2924g 34 1 the the DET c247dr2924g 34 2 ethyl ethyl PROPN c247dr2924g 34 3 ester ester PROPN c247dr2924g 34 4 substituted substituted PROPN c247dr2924g 34 5 case case NOUN c247dr2924g 34 6 has have AUX c247dr2924g 34 7 also also ADV c247dr2924g 34 8 been be AUX c247dr2924g 34 9 further far ADV c247dr2924g 34 10 established establish VERB c247dr2924g 34 11 using use VERB c247dr2924g 34 12 methyl methyl NOUN c247dr2924g 34 13 substituted substitute VERB c247dr2924g 34 14 homoallylic homoallylic NOUN c247dr2924g 34 15 alcohols alcohol NOUN c247dr2924g 34 16 showing show VERB c247dr2924g 34 17 that that SCONJ c247dr2924g 34 18 the the DET c247dr2924g 34 19 argument argument NOUN c247dr2924g 34 20 was be AUX c247dr2924g 34 21 universal universal ADJ c247dr2924g 34 22 . . PUNCT c247dr2924g 35 1 starting start VERB c247dr2924g 35 2 from from ADP c247dr2924g 35 3 the the DET c247dr2924g 35 4 homoallylic homoallylic NOUN c247dr2924g 35 5 alcohol alcohol NOUN c247dr2924g 35 6 we we PRON c247dr2924g 35 7 have have AUX c247dr2924g 35 8 established establish VERB c247dr2924g 35 9 a a DET c247dr2924g 35 10 four four NUM c247dr2924g 35 11 - - PUNCT c247dr2924g 35 12 step step NOUN c247dr2924g 35 13 sequence sequence NOUN c247dr2924g 35 14 to to PART c247dr2924g 35 15 give give VERB c247dr2924g 35 16 a a DET c247dr2924g 35 17 single single ADJ c247dr2924g 35 18 diastereomeric diastereomeric NOUN c247dr2924g 35 19 cyclopropane cyclopropane NOUN c247dr2924g 35 20 . . PUNCT c247dr2924g 36 1 the the DET c247dr2924g 36 2 method method NOUN c247dr2924g 36 3 is be AUX c247dr2924g 36 4 highlighted highlight VERB c247dr2924g 36 5 by by ADP c247dr2924g 36 6 the the DET c247dr2924g 36 7 rcm rcm NOUN c247dr2924g 36 8 strategy strategy NOUN c247dr2924g 36 9 and and CCONJ c247dr2924g 36 10 has have AUX c247dr2924g 36 11 shown show VERB c247dr2924g 36 12 to to PART c247dr2924g 36 13 be be AUX c247dr2924g 36 14 quite quite ADV c247dr2924g 36 15 robust robust ADJ c247dr2924g 36 16 . . PUNCT c247dr2924g 37 1 after after ADP c247dr2924g 37 2 finishing finish VERB c247dr2924g 37 3 the the DET c247dr2924g 37 4 trisubstituted trisubstitute VERB c247dr2924g 37 5 cyclopropane cyclopropane NOUN c247dr2924g 37 6 work work NOUN c247dr2924g 37 7 we we PRON c247dr2924g 37 8 looked look VERB c247dr2924g 37 9 back back ADV c247dr2924g 37 10 into into ADP c247dr2924g 37 11 the the DET c247dr2924g 37 12 sequence sequence NOUN c247dr2924g 37 13 at at ADP c247dr2924g 37 14 our our PRON c247dr2924g 37 15 silyloxycycloheptene silyloxycycloheptene ADJ c247dr2924g 37 16 intermediates intermediate NOUN c247dr2924g 37 17 and and CCONJ c247dr2924g 37 18 realized realize VERB c247dr2924g 37 19 that that SCONJ c247dr2924g 37 20 within within ADP c247dr2924g 37 21 the the DET c247dr2924g 37 22 molecule molecule NOUN c247dr2924g 37 23 laid lay VERB c247dr2924g 37 24 a a DET c247dr2924g 37 25 latent latent ADJ c247dr2924g 37 26 homoallylic homoallylic NOUN c247dr2924g 37 27 alcohol alcohol NOUN c247dr2924g 37 28 with with ADP c247dr2924g 37 29 a a DET c247dr2924g 37 30 ? ? PROPN c247dr2924g 37 31 -silyl -silyl PROPN c247dr2924g 37 32 group group NOUN c247dr2924g 37 33 . . PUNCT c247dr2924g 38 1 this this PRON c247dr2924g 38 2 is be AUX c247dr2924g 38 3 shown show VERB c247dr2924g 38 4 when when SCONJ c247dr2924g 38 5 we we PRON c247dr2924g 38 6 took take VERB c247dr2924g 38 7 the the DET c247dr2924g 38 8 intermediate intermediate ADJ c247dr2924g 38 9 and and CCONJ c247dr2924g 38 10 reduced reduce VERB c247dr2924g 38 11 the the DET c247dr2924g 38 12 ethyl ethyl PROPN c247dr2924g 38 13 ester ester PROPN c247dr2924g 38 14 to to ADP c247dr2924g 38 15 the the DET c247dr2924g 38 16 corresponding corresponding ADJ c247dr2924g 38 17 primary primary ADJ c247dr2924g 38 18 alcohol alcohol PROPN c247dr2924g 38 19 . . PUNCT c247dr2924g 39 1 this this DET c247dr2924g 39 2 reaction reaction NOUN c247dr2924g 39 3 was be AUX c247dr2924g 39 4 carried carry VERB c247dr2924g 39 5 out out ADP c247dr2924g 39 6 at at ADP c247dr2924g 39 7 low low ADJ c247dr2924g 39 8 temperature temperature NOUN c247dr2924g 39 9 to to PART c247dr2924g 39 10 ensure ensure VERB c247dr2924g 39 11 that that SCONJ c247dr2924g 39 12 silicon silicon NOUN c247dr2924g 39 13 - - PUNCT c247dr2924g 39 14 oxygen oxygen NOUN c247dr2924g 39 15 bond bond NOUN c247dr2924g 39 16 cleavage cleavage NOUN c247dr2924g 39 17 did do AUX c247dr2924g 39 18 not not PART c247dr2924g 39 19 occur occur VERB c247dr2924g 39 20 . . PUNCT c247dr2924g 40 1 with with ADP c247dr2924g 40 2 the the DET c247dr2924g 40 3 silyloxy silyloxy PROPN c247dr2924g 40 4 ring ring NOUN c247dr2924g 40 5 intact intact ADJ c247dr2924g 41 1 we we PRON c247dr2924g 41 2 activated activate VERB c247dr2924g 41 3 the the DET c247dr2924g 41 4 primary primary ADJ c247dr2924g 41 5 hydroxy hydroxy NOUN c247dr2924g 41 6 and and CCONJ c247dr2924g 41 7 the the DET c247dr2924g 41 8 cyclopropanation cyclopropanation NOUN c247dr2924g 41 9 took take VERB c247dr2924g 41 10 place place NOUN c247dr2924g 41 11 to to PART c247dr2924g 41 12 afford afford VERB c247dr2924g 41 13 a a DET c247dr2924g 41 14 disubstituted disubstituted ADJ c247dr2924g 41 15 cyclopropane cyclopropane NOUN c247dr2924g 41 16 with with ADP c247dr2924g 41 17 cis cis NOUN c247dr2924g 41 18 orientation orientation NOUN c247dr2924g 41 19 of of ADP c247dr2924g 41 20 the the DET c247dr2924g 41 21 two two NUM c247dr2924g 41 22 substituents substituent NOUN c247dr2924g 41 23 . . PUNCT c247dr2924g 42 1 we we PRON c247dr2924g 42 2 then then ADV c247dr2924g 42 3 took take VERB c247dr2924g 42 4 the the DET c247dr2924g 42 5 same same ADJ c247dr2924g 42 6 intermediate intermediate ADJ c247dr2924g 42 7 and and CCONJ c247dr2924g 42 8 treated treat VERB c247dr2924g 42 9 it it PRON c247dr2924g 42 10 with with ADP c247dr2924g 42 11 excess excess ADJ c247dr2924g 42 12 lah lah NOUN c247dr2924g 42 13 which which PRON c247dr2924g 42 14 provided provide VERB c247dr2924g 42 15 the the DET c247dr2924g 42 16 corresponding corresponding ADJ c247dr2924g 42 17 diol diol NOUN c247dr2924g 42 18 from from ADP c247dr2924g 42 19 reduction reduction NOUN c247dr2924g 42 20 of of ADP c247dr2924g 42 21 the the DET c247dr2924g 42 22 ester ester NOUN c247dr2924g 42 23 followed follow VERB c247dr2924g 42 24 by by ADP c247dr2924g 42 25 silicon silicon NOUN c247dr2924g 42 26 - - PUNCT c247dr2924g 42 27 oxygen oxygen NOUN c247dr2924g 42 28 bond bond NOUN c247dr2924g 42 29 cleavage cleavage NOUN c247dr2924g 42 30 . . PUNCT c247dr2924g 43 1 this this DET c247dr2924g 43 2 molecule molecule NOUN c247dr2924g 43 3 was be AUX c247dr2924g 43 4 activated activate VERB c247dr2924g 43 5 using use VERB c247dr2924g 43 6 standard standard ADJ c247dr2924g 43 7 conditions condition NOUN c247dr2924g 43 8 and and CCONJ c247dr2924g 43 9 cleanly cleanly ADV c247dr2924g 43 10 yielded yield VERB c247dr2924g 43 11 a a DET c247dr2924g 43 12 disubstituted disubstituted ADJ c247dr2924g 43 13 cyclopropane cyclopropane NOUN c247dr2924g 43 14 where where SCONJ c247dr2924g 43 15 the the DET c247dr2924g 43 16 orientation orientation NOUN c247dr2924g 43 17 of of ADP c247dr2924g 43 18 the the DET c247dr2924g 43 19 two two NUM c247dr2924g 43 20 groups group NOUN c247dr2924g 43 21 were be AUX c247dr2924g 43 22 trans trans ADJ c247dr2924g 43 23 to to ADP c247dr2924g 43 24 each each DET c247dr2924g 43 25 other other ADJ c247dr2924g 43 26 . . PUNCT c247dr2924g 44 1 this this DET c247dr2924g 44 2 second second ADJ c247dr2924g 44 3 case case NOUN c247dr2924g 44 4 once once ADV c247dr2924g 44 5 again again ADV c247dr2924g 44 6 proved prove VERB c247dr2924g 44 7 the the DET c247dr2924g 44 8 a a DET c247dr2924g 44 9 - - PUNCT c247dr2924g 44 10 strain strain NOUN c247dr2924g 44 11 argument argument NOUN c247dr2924g 44 12 . . PUNCT c247dr2924g 45 1 we we PRON c247dr2924g 45 2 have have AUX c247dr2924g 45 3 proposed propose VERB c247dr2924g 45 4 that that SCONJ c247dr2924g 45 5 the the DET c247dr2924g 45 6 reason reason NOUN c247dr2924g 45 7 for for SCONJ c247dr2924g 45 8 the the DET c247dr2924g 45 9 diol diol NOUN c247dr2924g 45 10 to to PART c247dr2924g 45 11 afford afford VERB c247dr2924g 45 12 a a DET c247dr2924g 45 13 cyclopropane cyclopropane NOUN c247dr2924g 45 14 of of ADP c247dr2924g 45 15 trans trans PROPN c247dr2924g 45 16 stereochemistry stereochemistry NOUN c247dr2924g 45 17 was be AUX c247dr2924g 45 18 because because SCONJ c247dr2924g 45 19 of of ADP c247dr2924g 45 20 the the DET c247dr2924g 45 21 steric steric ADJ c247dr2924g 45 22 environment environment NOUN c247dr2924g 45 23 during during ADP c247dr2924g 45 24 the the DET c247dr2924g 45 25 carbon carbon NOUN c247dr2924g 45 26 - - PUNCT c247dr2924g 45 27 carbon carbon NOUN c247dr2924g 45 28 forming forming NOUN c247dr2924g 45 29 step step NOUN c247dr2924g 45 30 . . PUNCT c247dr2924g 46 1 we we PRON c247dr2924g 46 2 have have AUX c247dr2924g 46 3 postulated postulate VERB c247dr2924g 46 4 that that SCONJ c247dr2924g 46 5 the the DET c247dr2924g 46 6 olefin olefin NOUN c247dr2924g 46 7 and and CCONJ c247dr2924g 46 8 the the DET c247dr2924g 46 9 ? ? PROPN c247dr2924g 46 10 -hydrogen -hydrogen X c247dr2924g 46 11 are be AUX c247dr2924g 46 12 eclipsed eclipse VERB c247dr2924g 46 13 or or CCONJ c247dr2924g 46 14 in in ADP c247dr2924g 46 15 other other ADJ c247dr2924g 46 16 words word NOUN c247dr2924g 46 17 , , PUNCT c247dr2924g 46 18 that that SCONJ c247dr2924g 46 19 the the DET c247dr2924g 46 20 group group NOUN c247dr2924g 46 21 containing contain VERB c247dr2924g 46 22 the the DET c247dr2924g 46 23 secondary secondary ADJ c247dr2924g 46 24 hydroxyl hydroxyl PROPN c247dr2924g 46 25 and and CCONJ c247dr2924g 46 26 the the DET c247dr2924g 46 27 olefin olefin NOUN c247dr2924g 46 28 oppose oppose VERB c247dr2924g 46 29 each each DET c247dr2924g 46 30 other other ADJ c247dr2924g 46 31 . . PUNCT c247dr2924g 47 1 this this DET c247dr2924g 47 2 theory theory NOUN c247dr2924g 47 3 is be AUX c247dr2924g 47 4 in in ADP c247dr2924g 47 5 concert concert NOUN c247dr2924g 47 6 with with ADP c247dr2924g 47 7 the the DET c247dr2924g 47 8 transition transition NOUN c247dr2924g 47 9 states state NOUN c247dr2924g 47 10 we we PRON c247dr2924g 47 11 have have AUX c247dr2924g 47 12 seen see VERB c247dr2924g 47 13 before before ADV c247dr2924g 47 14 in in ADP c247dr2924g 47 15 the the DET c247dr2924g 47 16 trisubstituted trisubstitute VERB c247dr2924g 47 17 case case NOUN c247dr2924g 47 18 where where SCONJ c247dr2924g 47 19 the the DET c247dr2924g 47 20 1,3 1,3 PROPN c247dr2924g 47 21 interaction interaction NOUN c247dr2924g 47 22 is be AUX c247dr2924g 47 23 the the DET c247dr2924g 47 24 dominant dominant ADJ c247dr2924g 47 25 force force NOUN c247dr2924g 47 26 . . PUNCT c247dr2924g 48 1 all all DET c247dr2924g 48 2 this this DET c247dr2924g 48 3 work work NOUN c247dr2924g 48 4 was be AUX c247dr2924g 48 5 published publish VERB c247dr2924g 48 6 in in ADP c247dr2924g 48 7 organic organic ADJ c247dr2924g 48 8 letters letter NOUN c247dr2924g 48 9 , , PUNCT c247dr2924g 48 10 vol vol NOUN c247dr2924g 48 11 . . PROPN c247dr2924g 49 1 2 2 NUM c247dr2924g 49 2 , , PUNCT c247dr2924g 49 3 no no NOUN c247dr2924g 49 4 . . NOUN c247dr2924g 49 5 5 5 NUM c247dr2924g 49 6 , , PUNCT c247dr2924g 49 7 601 601 NUM c247dr2924g 49 8 - - SYM c247dr2924g 49 9 603 603 NUM c247dr2924g 49 10 . . PUNCT c247dr2924g 50 1 the the DET c247dr2924g 50 2 paper paper NOUN c247dr2924g 50 3 summarizes summarize VERB c247dr2924g 50 4 the the DET c247dr2924g 50 5 work work NOUN c247dr2924g 50 6 that that PRON c247dr2924g 50 7 used use VERB c247dr2924g 50 8 the the DET c247dr2924g 50 9 rcm rcm NOUN c247dr2924g 50 10 strategy strategy NOUN c247dr2924g 50 11 for for ADP c247dr2924g 50 12 the the DET c247dr2924g 50 13 synthesis synthesis NOUN c247dr2924g 50 14 of of ADP c247dr2924g 50 15 trisubstituted trisubstitute VERB c247dr2924g 50 16 cyclopropanes cyclopropane NOUN c247dr2924g 50 17 and and CCONJ c247dr2924g 50 18 disubstituted disubstitute VERB c247dr2924g 50 19 cyclopropanes cyclopropane NOUN c247dr2924g 50 20 of of ADP c247dr2924g 50 21 both both CCONJ c247dr2924g 50 22 cis cis NOUN c247dr2924g 50 23 and and CCONJ c247dr2924g 50 24 trans trans PROPN c247dr2924g 50 25 geometry geometry NOUN c247dr2924g 50 26 . . PUNCT c247dr2924g 51 1 our our PRON c247dr2924g 51 2 methodology methodology NOUN c247dr2924g 51 3 had have AUX c247dr2924g 51 4 now now ADV c247dr2924g 51 5 developed develop VERB c247dr2924g 51 6 from from ADP c247dr2924g 51 7 a a DET c247dr2924g 51 8 limited limited ADJ c247dr2924g 51 9 three three NUM c247dr2924g 51 10 - - PUNCT c247dr2924g 51 11 step step NOUN c247dr2924g 51 12 sequence sequence NOUN c247dr2924g 51 13 from from ADP c247dr2924g 51 14 epoxides epoxide NOUN c247dr2924g 51 15 to to ADP c247dr2924g 51 16 a a DET c247dr2924g 51 17 four four NUM c247dr2924g 51 18 - - PUNCT c247dr2924g 51 19 step step NOUN c247dr2924g 51 20 sequence sequence NOUN c247dr2924g 51 21 starting start VERB c247dr2924g 51 22 from from ADP c247dr2924g 51 23 a a DET c247dr2924g 51 24 homoallylic homoallylic ADJ c247dr2924g 51 25 alcohol alcohol NOUN c247dr2924g 51 26 that that PRON c247dr2924g 51 27 exploited exploit VERB c247dr2924g 51 28 the the DET c247dr2924g 51 29 rcm rcm NOUN c247dr2924g 51 30 reaction reaction NOUN c247dr2924g 51 31 with with ADP c247dr2924g 51 32 grubbs grubb NOUN c247dr2924g 51 33 ' ' PART c247dr2924g 51 34 ruthenium ruthenium NOUN c247dr2924g 51 35 catalyst catalyst NOUN c247dr2924g 51 36 . . PUNCT c247dr2924g 52 1 at at ADP c247dr2924g 52 2 this this DET c247dr2924g 52 3 time time NOUN c247dr2924g 52 4 grubbs grubb VERB c247dr2924g 52 5 et et PROPN c247dr2924g 52 6 . . PROPN c247dr2924g 52 7 al al PROPN c247dr2924g 52 8 . . PROPN c247dr2924g 52 9 began begin VERB c247dr2924g 52 10 publishing publish VERB c247dr2924g 52 11 on on ADP c247dr2924g 52 12 a a DET c247dr2924g 52 13 second second ADJ c247dr2924g 52 14 generation generation NOUN c247dr2924g 52 15 catalyst catalyst NOUN c247dr2924g 52 16 that that PRON c247dr2924g 52 17 was be AUX c247dr2924g 52 18 quite quite ADV c247dr2924g 52 19 promising promising ADJ c247dr2924g 52 20 for for ADP c247dr2924g 52 21 cross cross ADJ c247dr2924g 52 22 - - NOUN c247dr2924g 52 23 metathesis metathesis NOUN c247dr2924g 52 24 reactions reaction NOUN c247dr2924g 52 25 and and CCONJ c247dr2924g 52 26 exhibited exhibit VERB c247dr2924g 52 27 a a DET c247dr2924g 52 28 large large ADJ c247dr2924g 52 29 range range NOUN c247dr2924g 52 30 of of ADP c247dr2924g 52 31 functional functional ADJ c247dr2924g 52 32 group group NOUN c247dr2924g 52 33 compatibility compatibility NOUN c247dr2924g 52 34 . . PUNCT c247dr2924g 53 1 we we PRON c247dr2924g 53 2 chose choose VERB c247dr2924g 53 3 to to PART c247dr2924g 53 4 exploit exploit VERB c247dr2924g 53 5 the the DET c247dr2924g 53 6 new new ADJ c247dr2924g 53 7 catalyst catalyst NOUN c247dr2924g 53 8 for for ADP c247dr2924g 53 9 our our PRON c247dr2924g 53 10 third third ADJ c247dr2924g 53 11 generation generation NOUN c247dr2924g 53 12 synthesis synthesis NOUN c247dr2924g 53 13 of of ADP c247dr2924g 53 14 cyclopropanes cyclopropane NOUN c247dr2924g 53 15 . . PUNCT c247dr2924g 54 1 we we PRON c247dr2924g 54 2 envisioned envision VERB c247dr2924g 54 3 using use VERB c247dr2924g 54 4 allyltrimethylsilane allyltrimethylsilane NOUN c247dr2924g 54 5 and and CCONJ c247dr2924g 54 6 a a DET c247dr2924g 54 7 homoallylic homoallylic ADJ c247dr2924g 54 8 alcohol alcohol NOUN c247dr2924g 54 9 as as ADP c247dr2924g 54 10 coupling couple VERB c247dr2924g 54 11 partners partner NOUN c247dr2924g 54 12 in in ADP c247dr2924g 54 13 a a DET c247dr2924g 54 14 cross cross NOUN c247dr2924g 54 15 metathesis metathesis NOUN c247dr2924g 54 16 reaction reaction NOUN c247dr2924g 54 17 . . PUNCT c247dr2924g 55 1 we we PRON c247dr2924g 55 2 accomplished accomplish VERB c247dr2924g 55 3 crossing cross VERB c247dr2924g 55 4 both both PRON c247dr2924g 55 5 substituted substitute VERB c247dr2924g 55 6 and and CCONJ c247dr2924g 55 7 simple simple ADJ c247dr2924g 55 8 homoallylic homoallylic NOUN c247dr2924g 55 9 alcohols alcohol NOUN c247dr2924g 55 10 with with ADP c247dr2924g 55 11 allyltrimethylsilane allyltrimethylsilane PROPN c247dr2924g 55 12 using use VERB c247dr2924g 55 13 the the DET c247dr2924g 55 14 new new ADJ c247dr2924g 55 15 grubbs grubb NOUN c247dr2924g 55 16 ' ' PART c247dr2924g 55 17 catalyst catalyst NOUN c247dr2924g 55 18 in in ADP c247dr2924g 55 19 yields yield NOUN c247dr2924g 55 20 ranging range VERB c247dr2924g 55 21 from from ADP c247dr2924g 55 22 70 70 NUM c247dr2924g 55 23 % % NOUN c247dr2924g 55 24 to to PART c247dr2924g 55 25 95 95 NUM c247dr2924g 55 26 % % NOUN c247dr2924g 55 27 . . PUNCT c247dr2924g 56 1 this this DET c247dr2924g 56 2 new new ADJ c247dr2924g 56 3 procedure procedure NOUN c247dr2924g 56 4 was be AUX c247dr2924g 56 5 then then ADV c247dr2924g 56 6 used use VERB c247dr2924g 56 7 to to PART c247dr2924g 56 8 make make VERB c247dr2924g 56 9 all all DET c247dr2924g 56 10 the the DET c247dr2924g 56 11 cyclopropanes cyclopropane NOUN c247dr2924g 56 12 previously previously ADV c247dr2924g 56 13 published publish VERB c247dr2924g 56 14 . . PUNCT c247dr2924g 57 1 however however ADV c247dr2924g 57 2 , , PUNCT c247dr2924g 57 3 during during ADP c247dr2924g 57 4 the the DET c247dr2924g 57 5 development development NOUN c247dr2924g 57 6 of of ADP c247dr2924g 57 7 this this DET c247dr2924g 57 8 two two NUM c247dr2924g 57 9 step step NOUN c247dr2924g 57 10 method method NOUN c247dr2924g 57 11 we we PRON c247dr2924g 57 12 found find VERB c247dr2924g 57 13 that that SCONJ c247dr2924g 57 14 when when SCONJ c247dr2924g 57 15 the the DET c247dr2924g 57 16 cyclopropane cyclopropane NOUN c247dr2924g 57 17 precursor precursor NOUN c247dr2924g 57 18 of of ADP c247dr2924g 57 19 substituted substituted ADJ c247dr2924g 57 20 alcohols alcohol NOUN c247dr2924g 57 21 was be AUX c247dr2924g 57 22 activated activate VERB c247dr2924g 57 23 we we PRON c247dr2924g 57 24 got get VERB c247dr2924g 57 25 a a DET c247dr2924g 57 26 50:50 50:50 NUM c247dr2924g 57 27 mixture mixture NOUN c247dr2924g 57 28 of of ADP c247dr2924g 57 29 desired desire VERB c247dr2924g 57 30 cyclopropane cyclopropane NOUN c247dr2924g 57 31 and and CCONJ c247dr2924g 57 32 trimethylsilane trimethylsilane NOUN c247dr2924g 57 33 protected protect VERB c247dr2924g 57 34 starting start VERB c247dr2924g 57 35 material material NOUN c247dr2924g 57 36 . . PUNCT c247dr2924g 58 1 previously previously ADV c247dr2924g 58 2 we we PRON c247dr2924g 58 3 did do AUX c247dr2924g 58 4 not not PART c247dr2924g 58 5 encounter encounter VERB c247dr2924g 58 6 this this DET c247dr2924g 58 7 problem problem NOUN c247dr2924g 58 8 when when SCONJ c247dr2924g 58 9 the the DET c247dr2924g 58 10 fluorosilane fluorosilane NOUN c247dr2924g 58 11 was be AUX c247dr2924g 58 12 the the DET c247dr2924g 58 13 stabilizer stabilizer NOUN c247dr2924g 58 14 . . PUNCT c247dr2924g 59 1 since since SCONJ c247dr2924g 59 2 the the DET c247dr2924g 59 3 result result NOUN c247dr2924g 59 4 ruined ruin VERB c247dr2924g 59 5 the the DET c247dr2924g 59 6 efficacy efficacy NOUN c247dr2924g 59 7 of of ADP c247dr2924g 59 8 our our PRON c247dr2924g 59 9 route route NOUN c247dr2924g 59 10 we we PRON c247dr2924g 59 11 explored explore VERB c247dr2924g 59 12 other other ADJ c247dr2924g 59 13 activation activation NOUN c247dr2924g 59 14 conditions condition NOUN c247dr2924g 59 15 ( ( PUNCT c247dr2924g 59 16 table table NOUN c247dr2924g 59 17 # # NOUN c247dr2924g 59 18 ) ) PUNCT c247dr2924g 59 19 . . PUNCT c247dr2924g 60 1 after after ADP c247dr2924g 60 2 attempting attempt VERB c247dr2924g 60 3 multiple multiple ADJ c247dr2924g 60 4 conditions condition NOUN c247dr2924g 60 5 we we PRON c247dr2924g 60 6 found find VERB c247dr2924g 60 7 that that SCONJ c247dr2924g 60 8 thionyl thionyl ADJ c247dr2924g 60 9 chloride chloride NOUN c247dr2924g 60 10 at at ADP c247dr2924g 60 11 0o 0o PROPN c247dr2924g 60 12 c c PROPN c247dr2924g 60 13 in in ADP c247dr2924g 60 14 methylene methylene PROPN c247dr2924g 60 15 chloride chloride PROPN c247dr2924g 60 16 was be AUX c247dr2924g 60 17 a a DET c247dr2924g 60 18 viable viable ADJ c247dr2924g 60 19 substitute substitute NOUN c247dr2924g 60 20 . . PUNCT c247dr2924g 61 1 with with ADP c247dr2924g 61 2 these these DET c247dr2924g 61 3 new new ADJ c247dr2924g 61 4 activating activating NOUN c247dr2924g 61 5 conditions condition NOUN c247dr2924g 61 6 we we PRON c247dr2924g 61 7 then then ADV c247dr2924g 61 8 were be AUX c247dr2924g 61 9 able able ADJ c247dr2924g 61 10 to to PART c247dr2924g 61 11 synthesis synthesis VERB c247dr2924g 61 12 a a DET c247dr2924g 61 13 variety variety NOUN c247dr2924g 61 14 of of ADP c247dr2924g 61 15 cyclopropanes cyclopropane NOUN c247dr2924g 61 16 , , PUNCT c247dr2924g 61 17 both both PRON c247dr2924g 61 18 disubstituted disubstitute VERB c247dr2924g 61 19 and and CCONJ c247dr2924g 61 20 trisubstituted trisubstitute VERB c247dr2924g 61 21 . . PUNCT c247dr2924g 62 1 we we PRON c247dr2924g 62 2 have have AUX c247dr2924g 62 3 now now ADV c247dr2924g 62 4 shown show VERB c247dr2924g 62 5 that that SCONJ c247dr2924g 62 6 cyclopropanes cyclopropane NOUN c247dr2924g 62 7 can can AUX c247dr2924g 62 8 be be AUX c247dr2924g 62 9 synthesized synthesize VERB c247dr2924g 62 10 in in ADP c247dr2924g 62 11 two two NUM c247dr2924g 62 12 steps step NOUN c247dr2924g 62 13 from from ADP c247dr2924g 62 14 a a DET c247dr2924g 62 15 variety variety NOUN c247dr2924g 62 16 of of ADP c247dr2924g 62 17 homoallylic homoallylic ADJ c247dr2924g 62 18 alcohols alcohol NOUN c247dr2924g 62 19 . . PUNCT c247dr2924g 63 1 we we PRON c247dr2924g 63 2 have have AUX c247dr2924g 63 3 demonstrated demonstrate VERB c247dr2924g 63 4 the the DET c247dr2924g 63 5 viability viability NOUN c247dr2924g 63 6 of of ADP c247dr2924g 63 7 the the DET c247dr2924g 63 8 grubbs grubb NOUN c247dr2924g 63 9 ' ' PART c247dr2924g 63 10 catalyst catalyst NOUN c247dr2924g 63 11 for for ADP c247dr2924g 63 12 the the DET c247dr2924g 63 13 cross cross NOUN c247dr2924g 63 14 - - NOUN c247dr2924g 63 15 metathesis metathesis NOUN c247dr2924g 63 16 of of ADP c247dr2924g 63 17 allyltrimethylsilane allyltrimethylsilane PROPN c247dr2924g 63 18 and and CCONJ c247dr2924g 63 19 varied varied ADJ c247dr2924g 63 20 homoallylic homoallylic NOUN c247dr2924g 63 21 alcohols alcohol NOUN c247dr2924g 63 22 . . PUNCT c247dr2924g 64 1 we we PRON c247dr2924g 64 2 have have AUX c247dr2924g 64 3 also also ADV c247dr2924g 64 4 shown show VERB c247dr2924g 64 5 that that SCONJ c247dr2924g 64 6 thionyl thionyl ADJ c247dr2924g 64 7 chloride chloride NOUN c247dr2924g 64 8 is be AUX c247dr2924g 64 9 an an DET c247dr2924g 64 10 excellent excellent ADJ c247dr2924g 64 11 reagent reagent NOUN c247dr2924g 64 12 for for ADP c247dr2924g 64 13 the the DET c247dr2924g 64 14 activation activation NOUN c247dr2924g 64 15 of of ADP c247dr2924g 64 16 the the DET c247dr2924g 64 17 cyclopropane cyclopropane NOUN c247dr2924g 64 18 precursor precursor NOUN c247dr2924g 64 19 . . PUNCT c247dr2924g 65 1 all all DET c247dr2924g 65 2 this this DET c247dr2924g 65 3 data datum NOUN c247dr2924g 65 4 was be AUX c247dr2924g 65 5 published publish VERB c247dr2924g 65 6 as as ADP c247dr2924g 65 7 a a DET c247dr2924g 65 8 full full ADJ c247dr2924g 65 9 paper paper NOUN c247dr2924g 65 10 in in ADP c247dr2924g 65 11 the the DET c247dr2924g 65 12 journal journal NOUN c247dr2924g 65 13 of of ADP c247dr2924g 65 14 the the DET c247dr2924g 65 15 american american PROPN c247dr2924g 65 16 chemical chemical PROPN c247dr2924g 65 17 society society NOUN c247dr2924g 65 18 . . PUNCT