Asymmetric Organocatalytic Epoxidations: Reactions, Scope, Mechanisms, and Applications

• Published in: Angewandte Chemie (International ed.) Vol. 53; no. 29; pp. 7406 - 7426
• Main Authors: Davis, Rebecca L., Stiller, Julian, Naicker, Tricia, Jiang, Hao, Jørgensen, Karl Anker
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 14.07.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Activation; Asymmetry; Carbonyl compounds; Catalysis; Catalysts; Epoxidation; Epoxy Compounds - chemistry; Expansion; Organic Chemicals - chemistry; organocatalysis; reaction mechanisms; small ring systems; Strain; Synthesis; synthetic methods; Unsaturated; organocatalysis; reaction mechanisms; epoxidation; small ring systems; synthetic methods
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201400241

Chiral epoxides serve as versatile building blocks in the synthesis of complex organic frameworks. The high strain imposed by the three‐membered ring system makes epoxides prone to a variety of nucleophilic ring‐opening reactions. Since the development of the Sharpless epoxidation, there have been many important contributions and advances in this area. With the rapid development of the field of asymmetric organocatalysis, a wide range of organocatalysts is now able to catalyze the epoxidation of broad class of unsaturated carbonyl compounds. In this Minireview, recent progress in the development of organocatalytic asymmetric epoxidation methods, the proposed mechanisms of these reactions and their applications as intermediates is reported. Pick your type: In the past several decades, highly useful epoxidation protocols have been developed with a variety of activation modes using a wide range of asymmetric organocatalysts. This review documents the rapid and expansive development in this area, thus providing a clear overview of the various catalyst types available for asymmetric organocatalytic epoxidations, as well as their mechanisms and applications.