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Enantioselective Baeyer-Villiger Oxidation: Desymmetrization of Meso Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones

Lin Zhou, Xiaohua Liu, Jie Ji, Yuheng Zhang, Xiaolei Hu, Lili Lin and Xiaoming Feng *

*Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China, Email: xmfengscu.edu.cn

L. Zhou, X. H. Liu, J. Ji, Y. H. Zhang, X. L. Hu, L. L. Lin, X. M. Feng, J. Am. Chem. Soc., 2012, 134, 17023-17026.

DOI: 10.1021/ja309262f (free Supporting Information)


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Abstract

Catalytic enantioselective Baeyer-Villiger oxidations of racemic and prochiral cyclic ketones were achieved in the presence of chiral N,N′-dioxide-ScIII complex catalysts. The oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active ε- and γ-lactones, respectively, in very good yields and up to 95% ee.

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Key Words

Baeyer-Villiger Oxidation, MCPBA


ID: J48-Y2012-3300