TY - JOUR
T1 - Stereoselective addition of lithium amides to activated triple bonds
AU - Feit, Ben Ami
AU - Dickerman, Shulamit
AU - Masrawe, Djamal
AU - Fishman, Ariela
PY - 1988
Y1 - 1988
N2 - The nucleophilic addition of R"2NLi to alkyl esters of R'C≡CO2R; (R' = H, CO2R; R = Me, Et) in apolar solvents, in the presence and in the absence of solvating agents, has been studied. The only or the main reaction product obtained under all experimental conditions was the corresponding (E)-R"2NCR'=CH-CO2R. It is suggested that the vinyl-lithium intermediate, which is first formed by an anti-type addition of R"2NLi to the triple bond, undergoes a very fast isomerisation, owing to the highly effective configurationally destabilising R+ effect of the electron-donating dialkylamino trans-β-substituent.
AB - The nucleophilic addition of R"2NLi to alkyl esters of R'C≡CO2R; (R' = H, CO2R; R = Me, Et) in apolar solvents, in the presence and in the absence of solvating agents, has been studied. The only or the main reaction product obtained under all experimental conditions was the corresponding (E)-R"2NCR'=CH-CO2R. It is suggested that the vinyl-lithium intermediate, which is first formed by an anti-type addition of R"2NLi to the triple bond, undergoes a very fast isomerisation, owing to the highly effective configurationally destabilising R+ effect of the electron-donating dialkylamino trans-β-substituent.
UR - http://www.scopus.com/inward/record.url?scp=37049078698&partnerID=8YFLogxK
U2 - 10.1039/p19880000927
DO - 10.1039/p19880000927
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AN - SCOPUS:37049078698
SP - 927
EP - 929
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 0300-922X
IS - 4
ER -