Z/E selective synthesis of β,β-disubstituted and (Z)-β- monosubstituted Baylis-Hillman adducts via anionic additions of vinylcuprates to aldehydes

Han Xun Wei, Steven Willis, Guigen Li

Research output: Contribution to journalArticle

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Abstract

A new method has been developed for the synthesis of achiral β,β- disubstituted and (Z)-β-monosubstituted Baylis-Hillman adducts with excellent Z/E stereospecificity in some cases. The process involves the conjugate additions of R2CuLi or RMgBr-CuBr-DMS to α,β-acetylenic esters and followed by additions of anionic α-(alkoxycarbonyl)vinyl]copper intermediates to aldehydes. The individual Z- and E- isomers of the resulting β-branched α-(hydroxylalkyl)acrylates can be separated by column chromatography in modest to excellent yield.

Original languageEnglish
Pages (from-to)2959-2966
Number of pages8
JournalSynthetic Communications
Volume29
Issue number17
DOIs
StatePublished - Jan 1 1999

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