Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.
In this communication, we describe the development of the first highly enantioselective catalytic conjugate addition to vinyl sulfones. Promoted by readily accessible organocatalysts derived from C6'-OH cinchona alkaloid derivatives and under mild, air- and moisture-tolerant conditions, conjugate additions of a wide range of alpha-cyanoacetates bearing either an alpha-aryl or an alpha-alkyl substituent to vinyl sulfones proceeded in excellent enantioselectivity and high yield. Consequently, this efficient and operationally simple enantioselective C-C bond forming conjugate addition provides a new and useful approach for the enantioselective construction of all-carbon quaternary stereocenters.
Li
Hongming
H
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Song
Jun
J
Liu
Xiaofeng
X
Deng
Li
L
D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D013450:Sulfones; D014753:Vinyl Compounds; D002244:Carbon