Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with <i>in situ</i> Generated <i>N</i>-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea

Abstract

Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable alpha-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active alpha,beta-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.

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