Stereoselective addition of lithium amides to activated triple bonds

Ben Ami Feit, Shulamit Dickerman, Djamal Masrawe, Ariela Fishman

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)927-929
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
DOIs
StatePublished - 1988

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