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Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System

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Abstract

The oxidative kinetic resolution of racemic secondary alcohols was efficiently catalyzed by a chiral Mn(III)–salen complex using sodium hypochlorite (NaClO) as an oxidant in the presence of 8 mol% N-bromosuccinimide (NBS) in a dichloromethylene-water mixture solvent at room temperature. Excellent ee’s (up to 99 %) of chiral secondary alcohols were achieved in most cases.

Graphical Abstract

Chiral Mn(III)–salen complex catalyzed oxidative kinetic resolution (OKR) of secondary alcohols has been achieved with sodium hypochlorite as an oxidant in the presence of a catalytic amount of N-bromosuccinimide. This novel protocol is very efficient for the OKR of a variety of secondary alcohols.

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Acknowledgments

The authors are grateful for financial support from the National Natural Science Foundation of China (no. 21276061) and the Natural Science Foundation of Hebei Province, China (no. B2013202158).

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Authors and Affiliations

  1. School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin, 300130, People’s Republic of China

    Yuecheng Zhang, Baosheng Gao, Qiao Zhou & Jiquan Zhao

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  1. Yuecheng Zhang
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  2. Baosheng Gao
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  3. Qiao Zhou
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  4. Jiquan Zhao
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Corresponding author

Correspondence to Jiquan Zhao.

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Zhang, Y., Gao, B., Zhou, Q. et al. Oxidative Kinetic Resolution of Secondary Alcohols with Salen–Mn(III)/NBS/NaClO System. Catal Lett 144, 1797–1802 (2014). https://doi.org/10.1007/s10562-014-1339-9

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  • DOI: https://doi.org/10.1007/s10562-014-1339-9

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