Cinchona-based Primary Amine Catalysis in the Asymmetric Functionalization of Carbonyl Compounds

Asymmetric aminocatalysis exploits the potential of chiral primary and secondary amines to catalyze asymmetric reactions. It has greatly simplified the functionalization of carbonyl compounds while ensuring high enantioselectivity. Recent advances in cinchona-based primary amine catalysis have provided new synthetic opportunities and conceptual perspectives for successfully attacking major challenges in carbonyl compound chemistry, which traditional approaches have not been able to address. This Review outlines the historical context for the development of this catalyst class while charting the landmark discoveries and applications that have further expanded the synthetic potential of aminocatalysis. Primary choice: In only five years, cinchona-based primary amine catalysis has almost equaled the high level of efficiency and reliability of aminocatalysis by proline-derived catalysts, offering the unique possibility of effecting reactions between sterically demanding carbonyl compounds (see picture). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.