title: Organocatalytic stereoselective epoxidation of trisubstituted acrylonitriles.
abstract: The first diastereospecific and enantioselective epoxidation of trans-2-aroyl-3-arylacrylonitriles by means of the commercially available diaryl L-prolinol/tert-butyl hydroperoxide system has been developed. These diversely functionalized epoxides were obtained in excellent yield (up to 99%), complete diastereoselectivity for the trans-isomer, and good enantioselectivity (up to 84% ee). Highly enantioenriched epoxides can be easily obtained after a single crystallization (ee > 90%).
authors.affiliation: Dipartimento di Chimica, Università di Salerno, Via Ponte don Melillo, 84084, Fisciano, Italy.
authors.forename: Claudia
authors.initials: C
authors.lastname: De Fusco
authors.forename: Consiglia
authors.initials: C
authors.lastname: Tedesco
authors.forename: Alessandra
authors.initials: A
authors.lastname: Lattanzi
mesh_terms: D000181:Acrylonitrile / Q000737:chemistry*; D002384:Catalysis; D003460:Crystallization; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014961:X-Ray Diffraction
chemical_list: D004852:Epoxy Compounds; D000181:Acrylonitrile