Catalytic Asymmetric Construction of Vicinal Tetrasubstituted Stereocenters by the Mannich Reaction of Linear α-Substituted Monothiomalonates with Isatin N-Boc Ketimines.

Abstract

A highly diastereo- and enantioselective method for the construction of vicinal tetrasubstituted stereocenters through the first catalytic asymmetric Mannich reaction of linear α-substituted MTMs with isatin N-Boc ketimines has been developed. This protocol provides atom-economic synthesis of less accessible 3-aminooxindoles bearing vicinal tetrasubstituted stereocenters. Notably, it also constitutes the first example of stereoselective synthesis of β-amino thioesters bearing vicinal tetrasubstituted stereocenters.