Overcoming the limitations of the Morita-Baylis-Hillman reaction: a rapid and general synthesis of alpha-alkenyl-beta'-hydroxy thioesters.
Acryloyl chlorides, aldehydes, and PhSLi undergo a direct aldol cascade sequence in the presence of MgBr2 x OEt2 via in situ derived thioester enolates, which is followed by oxidative elimination to give alpha-alkenyl-beta'-hydroxy thioesters. Overall, the procedure is rapid, efficient, and generally applicable, even to beta-substituted acryloyl chlorides, thus providing an alternative to the Morita-Baylis-Hillman reaction with substantially greater synthetic scope and utility.
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Emily
E
Tarsis
Anna
A
Gromova
Daniel
D
Lim
Guoqiang
G
Zhou
Don M
DM
Coltart
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
D000447:Aldehydes; D000475:Alkenes; D004952:Esters; D013438:Sulfhydryl Compounds; C116609:3-hydroxybutanal