Regio- and enantioselective conjugate addition of β-nitro α,β-unsaturated carbonyls to construct 3-alkenyl disubstituted oxindoles

Abstract

Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to β -nitroenones or β -nitroacrylates was established with chiral scandium catalysts. It enabled the construction of functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups in excellent yields and ee values. Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to β -nitroenones or β -nitroacrylates was established with chiral scandium catalysts. It enabled the construction of functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups in excellent yields and ee values.