Efficient enantioselective synthesis of trisubstituted γ-lactam via the Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media

Abstract

An efficient enantioselective Michael addition reaction of 2,3-dioxopyrrolidine with indole in aqueous media was developed by virtue of a chiral copper complex. This reaction features air tolerance, a broad substrate scope and mild reaction conditions. Furthermore, a gram-scale synthesis was conducted to afford the corresponding products with a high yield and excellent enantioselectivity. Moreover, the proposed mechanism was supported by control experiments, XPS investigation and DFT calculations.