Enantioselective Baeyer–Villiger oxidation: Desymmetrization of meso cyclic ketones and kinetic resolution of racemic 2-arylcyclohexanones

L Zhou, X Liu, J Ji, Y Zhang, X Hu, L Lin…

Index: Zhou, Lin; Liu, Xiaohua; Ji, Jie; Zhang, Yuheng; Hu, Xiaolei; Lin, Lili; Feng, Xiaoming Journal of the American Chemical Society, 2012 , vol. 134, # 41 p. 17023 - 17026,4

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Citation Number: 62

Abstract

Catalytic enantioselective Baeyer–Villiger (BV) oxidations of racemic and meso cyclic ketones were achieved in the presence of chiral N, N′-dioxide–ScIII complex catalysts. The BV oxidations of prochiral cyclohexanones and cyclobutanones afforded series of optically active ε-and γ-lactones, respectively, in up to 99% yield and 95% ee. Meanwhile, the kinetic resolution of racemic 2-arylcyclohexanones was also realized via an abnormal BV ...

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