Chiral Primary Amine Catalysis

Abstract

Aminocatalysis is a versatile catalytic motif for both nature and organocatalysis. While Nature’s aminoenzymes, e.g. Type I aldolase and decarboxylase, normally employ the primary amine group of lysine residue for catalysis, disproportionate emphasis has been placed on chiral secondary amines in organocatalysis due to the observed low activity in the initial attempt. Recently, there have been numerous exciting discoveries about the simple primary-amine organocatalysts. Beside their relevance in biomimetic catalysis and biogenesis, chiral primary aminocatalysis facilitates a range of transformation beyond the reach of secondary aminocatalysis. This review focuses on chiral primary amine catalysts, their history, catalytic features and applications as enamine, imminium and non-covalent catalysts.