title: Asymmetric organocatalytic epoxidations: reactions, scope, mechanisms, and applications.
abstract: 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.
authors.affiliation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark); Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, R3T 2N2 (Canada).
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Davis
authors.forename: Julian
authors.initials: J
authors.lastname: Stiller
authors.forename: Tricia
authors.initials: T
authors.lastname: Naicker
authors.forename: Hao
authors.initials: H
authors.lastname: Jiang
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D009930:Organic Chemicals
keywords: epoxidation; organocatalysis; reaction mechanisms; small ring systems; synthetic methods