Controllable Lewis Base Catalyzed Michael Addition of α-Amino­nitriles to Activated Alkenes: Facile Synthesis of Functionalized γ-Amino Acid Esters and γ-Lactams

Abstract

A novel protocol for the synthesis of functionalized γ-amino acid esters and γ-lactams through a controllable Lewis base catalyzed Michael addition of α-aminonitriles to simple activated alkenes has been developed. The scope, versatility, and efficiency of the process were demonstrated.

Ag-Catalyzed Cyanomethylation of Amines Using Nitromethane as a C1 Source

“…The structure has been identified in numerous bioactive compounds including pharmaceuticals . It has been applied as a useful building block for the formation of α-amino acids, β-aminoalcohols, 1,2-diamines, and so on. − The Strecker reaction, a traditional three-component condensation method, is the first choice for the preparation of α-amino nitriles. , Imine or iminium electrophiles generated in situ from amines and carbonyl compounds reacted with cyanide to afford the corresponding α-amino nitriles. However, this methodology is not suitable for the synthesis of N -tertiary α-amino nitriles from secondary amines .…”