title: Organocatalytic Asymmetric Reactions of Epoxides: Recent Progress.
abstract: In this Minireview recent advances in the asymmetric reactions of meso and racemic epoxides promoted by organocatalysts is reviewed. Organic promoters, such as chiral phosphoric acids, amino- and peptidyl thioureas, and sulfinamides, have been successfully used for a variety of enantioselective transformations of epoxides under catalytic conditions, involving direct nucleophilic attack at the oxirane ring, base-catalysed β-eliminations and Brønsted acid catalysed 1,2-rearrangements. Accordingly, highly valuable enantioenriched 1,2-functionalised alcohols, carbonyl compounds and nitroepoxides are attainable. Dual activation of the reagents, provided by the organocatalysts, appears to be the most recurrent strategy, potentially suitable to face other unmet challenges in asymmetric ring-opening reactions of epoxides.
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 84084, Fisciano, Italy.
authors.forename: Sara
authors.initials: S
authors.lastname: Meninno
authors.affiliation: Dipartimento di Chimica e Biologia "A. Zambelli", Università di Salerno, Via Giovanni Paolo II, 84084, Fisciano, Italy. lattanzi@unisa.it.
authors.forename: Alessandra
authors.identifier: http://orcid.org/0000-0003-1132-8610
authors.initials: A
authors.lastname: Lattanzi
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009930:Organic Chemicals; D010756:Phosphoric Acids / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D013890:Thiourea / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D009930:Organic Chemicals; D010756:Phosphoric Acids; D013449:Sulfonamides; D013890:Thiourea
keywords: desymmetrization; epoxides; kinetic resolution; organocatalysis; ring-opening reactions