Chiral primary amine mediated conjugate addition of branched aldehydes to vinyl sulfone: Asymmetric generation of quaternary carbon centers

Abstract

Novel l-threonine-derived bifunctional organic catalysts containing primary amine and sulfonamide groups were utilized to promote asymmetric conjugate addition of α,α-disubstitued 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. © 2010 The Royal Society of Chemistry.