High regio- and stereoselective Barbier reaction of carbonyl compounds mediated by NaBF4/Zn (Sn) in water

Zhenggen Zha; Zhen Xie; Cunliu Zhou; Mingxin Chang; Zhiyong Wang

doi:10.1039/B303187J

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High regio- and stereoselective Barbier reaction of carbonyl compounds mediated by NaBF₄/Zn (Sn) in water†

Zhenggen Zha,^a Zhen Xie,^a Cunliu Zhou,^a Mingxin Chang^a and Zhiyong Wang*^a

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* Corresponding authors

^a Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, China
E-mail: zwang3@ustc.edu.cn
Fax: +86 551 363 1760
Tel: +86 551 360 3185

Abstract

Studies with NaBF₄/M (M = Zn or Sn) showed that this novel mediator facilitated allylation of a variety of carbonyl compounds in water and had a great influence on the diastereoselectivity of the addition. More importantly, α- and γ-addition products of crotylations can be alternatively obtained under the control of this novel mediator. A reaction mechanism is proposed based on our quantum calculation and experimental results.

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Supplementary files

Spectral data of Barbier-type reaction products and quantum calculation results DOC (143K)

Article information

DOI: https://doi.org/10.1039/B303187J
Article type: Letter
Submitted: 20 Mar 2003
Accepted: 06 Jun 2003
First published: 24 Jul 2003

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New J. Chem., 2003,27, 1297-1300

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High regio- and stereoselective Barbier reaction of carbonyl compounds mediated by NaBF₄/Zn (Sn) in water

Z. Zha, Z. Xie, C. Zhou, M. Chang and Z. Wang, New J. Chem., 2003, 27, 1297 DOI: 10.1039/B303187J

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