TY - JOUR
T1 - Z/E selective synthesis of β,β-disubstituted and (Z)-β- monosubstituted Baylis-Hillman adducts via anionic additions of vinylcuprates to aldehydes
AU - Wei, Han Xun
AU - Willis, Steven
AU - Li, Guigen
N1 - Funding Information:
We gratefully acknowledge financial support from the Robert
PY - 1999
Y1 - 1999
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0032814468&partnerID=8YFLogxK
U2 - 10.1080/00397919908086469
DO - 10.1080/00397919908086469
M3 - Article
AN - SCOPUS:0032814468
SN - 0039-7911
VL - 29
SP - 2959
EP - 2966
JO - Synthetic Communications
JF - Synthetic Communications
IS - 17
ER -