Catalytic Efficiency of Primary β‐Amino Alcohols and Their Derivatives in Organocatalysis

Abstract

Chiral primary β‐amino alcohols, constuting adjacently positioned Brønsted base and Brønsted acid sites, are emerging as very valuable bifunctional organocatalysts in a wide array of asymmetric organic transformations. Primary β‐amino alcohols represent inexpensive alternatives to other primary amino organocatalysts such as chiral diamines and cinchona‐alkaloid‐derived primary amines, being easy to synthesize and air‐stable and offering the potential for introduction of different functional groups and also for alteration of steric sites. Here we reveal the catalytic use of simple primary β‐amino alcohols and their derivatives as organocatalysts in Diels–Alder cycloaddition, aldol condensation, Michael addition, 1,3‐dipolar cycloaddition, the Morita–Baylis–Hillman reaction, cascade cyclization, allylation of isatins, Friedel–Crafts alkylation and epoxidation of olefins.