Catalytic asymmetric desymmetrization of N-arylmaleimides: efficient construction of both atom chirality and axial chirality

Abstract

The catalytic asymmetric Michael addition/desymmetrization reaction of N-(2-t-butylphenyl)maleimides with unprotected 3-substituted-2-oxindoles was successfully realized using a chiral N,N'-dioxide-Sc(III) complex, leading to succinimides with two kinds of stereogenic elements—atom chirality and axial chirality—in up to 99% yield, 99% ee and >19 : 1 d.r.