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Asymmetric Organocatalytic Epoxidations: Reactions, Scope, Mechanisms, and Applications
Author(s) -
Davis Rebecca L.,
Stiller Julian,
Naicker Tricia,
Jiang Hao,
Jørgensen Karl Anker
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400241
Subject(s) - scope (computer science) , chemistry , organocatalysis , combinatorial chemistry , enantioselective synthesis , computer science , catalysis , organic chemistry , programming language
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.