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.
Zhu
Qiang
Q
Department of Chemistry, National University of Singapore, Republic of Singapore, 117543.
Lu
Yixin
Y
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