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Enantioselective α-Hydroxylation by Modified Salen-Zirconium(IV)-Catalyzed Oxidation of β-Keto Esters

Fan Yang, Jingnan Zhao, Xiaofei Tang, Guangli Zhou, Wangze Song and Qingwei Meng*

*State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, P. R. China, Email: mengqwdlut.edu.cn

F. Yang, J. Zhao, X. Tang, G. Zhou, W. Song, Q. Meng, Org. Lett., 2017, 19, 448-451.

DOI: 10.1021/acs.orglett.6b03554 (free Supporting Information)


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A chiral (1S,2S)-cyclohexanediamine backbone salen-zirconium(IV) complex as the catalyst enables a highly enantioselective α-hydroxylation of β-keto esters using cumene hydroperoxide (CHP) as the oxidant to provide chiral α-hydroxy β-keto esters in excellent yields and enantioselectivities. The zirconium catalyst is recyclable and the reaction can be performed in gram scale.

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Key Words

α-Hydroxylation, Indanones, CHP


ID: J54-Y2017