Chiral N,N′-dioxide–FeCl3 complex-catalyzed asymmetric intramolecular Cannizzaro reaction

Wangbin Wu; Xiaohua Liu; Yuheng Zhang; Jie Ji; Tianyu Huang; Lili Lin; Xiaoming Feng

doi:10.1039/C5CC04213E

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Chiral N,N′-dioxide–FeCl₃ complex-catalyzed asymmetric intramolecular Cannizzaro reaction†

Wangbin Wu,^a Xiaohua Liu,^a Yuheng Zhang,^a Jie Ji,^a Tianyu Huang,^a Lili Lin^a and Xiaoming Feng*^ab

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* Corresponding authors

^a Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
E-mail: 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 environmentally benign catalyst, the N,N′-dioxide–FeCl₃ complex, has been developed for the asymmetric intramolecular Cannizzaro reaction. Aryl and alkyl glyoxal monohydrates were applied to obtain α-hydroxy acid esters with excellent results. Deuterium-label and control experiments shed light on the reaction mechanism.

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Article information

DOI: https://doi.org/10.1039/C5CC04213E
Article type: Communication
Submitted: 21 May 2015
Accepted: 12 Jun 2015
First published: 22 Jun 2015

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Chem. Commun., 2015,51, 11646-11649

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Chiral N,N′-dioxide–FeCl₃ complex-catalyzed asymmetric intramolecular Cannizzaro reaction

W. Wu, X. Liu, Y. Zhang, J. Ji, T. Huang, L. Lin and X. Feng, Chem. Commun., 2015, 51, 11646 DOI: 10.1039/C5CC04213E

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