Regio- and enantioselective Baeyer-Villiger oxidation: kinetic resolution of racemic 2-substituted cyclopentanones

Lin Zhou; Xiaohua Liu; Jie Ji; Yuheng Zhang; Wangbin Wu; Yangbin Liu; Lili Lin; Xiaoming Feng

doi:10.1021/ol501737a

Regio- and enantioselective Baeyer-Villiger oxidation: kinetic resolution of racemic 2-substituted cyclopentanones

Org Lett. 2014 Aug 1;16(15):3938-41. doi: 10.1021/ol501737a. Epub 2014 Jul 16.

Authors

Lin Zhou¹, Xiaohua Liu, Jie Ji, Yuheng Zhang, Wangbin Wu, Yangbin Liu, Lili Lin, Xiaoming Feng

Affiliation

¹ Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, P. R. China.

PMID: 25029483
DOI: 10.1021/ol501737a

Abstract

A kinetic resolution of racemic 2-substituted cyclopentanones via highly regio- and enantioselective Baeyer-Villiger oxidation has been successfully developed. The reaction could afford the normal 6-substituted δ-lactones in up to 98% ee and >19/1 regioselectivity. Meanwhile, the unreacted ketones were recovered in excellent ee values (up to 98%). It represents the best results of the kinetic resolution of racemic 2-substituted cyclopentanones via nonenzymic asymmetric BV oxidation.