Chiral Primary Amine/Ketone Cooperative Catalysis for Asymmetric α-Hydroxylation with Hydrogen Peroxide

Mao Cai, Kaini Xu, Yuze Li, Zongxiu Nie, Long Zhang* and Sanzhong Luo*

*Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing 100084, China, Email: zhanglongtsinghua.edu.cn, luosztsinghua.edu.cn

M. Cai, K. Xu, Y. Li, Z. Nie, L. Zhang, S. Luo, J. Am. Chem. Soc., 2021, 143, 1078-1087.

DOI: 10.1021/jacs.0c11787

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Abstract

A cooperative primary amine and ketone dual catalytic approach enables the asymmetric α-hydroxylation of β-ketocarbonyls with H₂O₂ in excellent yield and enantioselectivity. Notably, late-stage hydroxylation for peptidyl amide or chiral esters can also be achieved with high stereoselectivity.

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proposed mechanism

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Key Words

hydroxylation, organocatalysis, hydrogen peroxide

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ID: J48-Y2021