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

Article abstract of DOI:10.1080/00397919908086469

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.

Full text of DOI:10.1080/00397919908086469

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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 a , Steven Willis a & Guigen Li a
a Department of Chemistry and Biochemistry , Texas Tech
University , Lubbock, TX, 79409-1061, USA
Published online: 25 Sep 2007.
To cite this article: Han-Xun Wei , Steven Willis & Guigen Li (1999) Z/E Selective Synthesis
of β,β-Disubstituted and (Z)-β-Monosubstituted Baylis-Hillman Adducts Via Anionic
Additions of Vinylcuprates to Aldehydes, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 29:17, 2959-2966, DOI:
10.1080/00397919908086469
To link to this article: http://dx.doi.org/10.1080/00397919908086469
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