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

Citation
Hx. Wei et al., Z/E selective synthesis of beta,beta-disubstituted and (Z)-beta-monosubstituted Baylis-Hillman adducts via anionic additions of vinylcuprates to aldehydes, SYN COMMUN, 29(17), 1999, pp. 2959-2966
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
17
Year of publication
1999
Pages
2959 - 2966
Database
ISI
SICI code
0039-7911(1999)29:17<2959:ZSSOBA>2.0.ZU;2-6
Abstract
A new method has been developed for the synthesis of achiral beta,beta-disu bstituted and (Z)-beta-monosubstituted Baylis-Hillman adducts with excellen t Z/E stereospecificity in some cases. The process involves the conjugate a dditions of R2CuLi or RMgBr-CuBr-DMS to alpha,beta-acetylenic esters and fo llowed by additions of anionic alpha-(alkoxycarbonyl)vinyl]copper intermedi ates to aldehydes. The individual Z- and E- isomers of the resulting beta-b ranched alpha-(hydroxylalkyl)acrylates can be separated by column chromatog raphy in modest to excellent yield.