Asymmetric Epoxidation Catalyzed by N-Aryl-Substituted Oxazolidinone-Containing Ketones:  Further Evidence for Electronic Effects

• Published in: Organic letters Vol. 5; no. 3; pp. 293 - 296
• Main Authors: Shu, Lianhe, Wang, Pingzhen, Gan, Yonghong, Shi, Yian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.02.2003; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Electrons; Ketones - chemistry; Molecular Structure; Oxazolidinones - chemistry; Oxidation-Reduction; Physical Sciences; Science & Technology; UNFUNCTIONALIZED OLEFINS; CHIRAL KETONES; GENERATED IN-SITU; HIGHLY ENANTIOSELECTIVE EPOXIDATION; DIOXIRANES; OXIDATIONS; CHEMISTRY; ALKENE EPOXIDATION; EFFICIENCY; OXONE
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol020229e

Ketones containing N-aryl-substituted oxazolidinones have been prepared and investigated for the epoxidation of cis-β-methylstyrene, styrene, and 1-phenylcyclohexene. The attractive interaction between the phenyl group of the olefin and the oxazolidinone of the catalyst is enhanced by introducing an electron-withdrawing group onto the N-phenyl group of the catalyst. The information obtained gives a better understanding of the ketone-catalyzed epoxidation. In addition, the easy preparation of some of the ketones makes them good candidates for practical use.