Catalytic asymmetric Meerwein–Ponndorf–Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex

Wangbin Wu; Sijia Zou; Lili Lin; Jie Ji; Yuheng Zhang; Baiwei Ma; Xiaohua Liu; Xiaoming Feng

doi:10.1039/C7CC00273D

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Catalytic asymmetric Meerwein–Ponndorf–Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)₃ complex†

Wangbin Wu,

^a Sijia Zou,

^a Lili Lin,

*^a Jie Ji,

^a Yuheng Zhang,

^a Baiwei Ma,

^a Xiaohua Liu

^a and Xiaoming Feng

*^ab

Author affiliations

* Corresponding authors

^a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
E-mail: lililin@scu.edu.cn, xmfeng@scu.edu.cn
Fax: +86 28 85418249
Tel: +86 28 85418249

^b Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, P. R. China

Abstract

An asymmetric Meerwein–Ponndorf–Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N′-dioxide/Y(OTf)₃ complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.

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Article information

DOI: https://doi.org/10.1039/C7CC00273D
Article type: Communication
Submitted: 12 Jan 2017
Accepted: 22 Feb 2017
First published: 23 Feb 2017

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Chem. Commun., 2017,53, 3232-3235

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Catalytic asymmetric Meerwein–Ponndorf–Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)₃ complex

W. Wu, S. Zou, L. Lin, J. Ji, Y. Zhang, B. Ma, X. Liu and X. Feng, Chem. Commun., 2017, 53, 3232 DOI: 10.1039/C7CC00273D

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