Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: asymmetric generation of quaternary carbon centers.
Novel L-threonine-derived bifunctional organic catalysts containing primary amine and sulfonamide groups were utilized to promote asymmetric conjugate addition of alpha,alpha-disubstituted aldehydes to 1,1-bis(benzenesulfonyl)ethylene. The adducts with quaternary stereogenic centers adjacent to an aldehyde group were obtained in high yield and with good enantioselectivity.
Department of Chemistry, National University of Singapore, Republic of Singapore, 117543.
Qiang
Q
Zhu
Yixin
Y
Lu
D000447:Aldehydes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D013912:Threonine / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D013450:Sulfones; D013912:Threonine; C009873:divinyl sulfone; D002244:Carbon