Issue 9, 2011
From the journal:

Chemical Science

Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center†

Hui Li,a   Fu-Min Zhang,a   Yong-Qiang Tu,*a   Qing-Wei Zhang,a   Zhi-Min Chen,a   Zhi-Hua Chena  and  Jian Lia  

* Corresponding authors

a State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, China
E-mail: tuyq@lzu.edu.cn.
Fax: (+86) 0931-8912582

Abstract

A bromination/semipinacol rearrangement reaction catalyzed by cinchona alkaloid derivatives was developed. With 5 mol% (DHQD)2PYDZ, β-bromoketones containing an all-α-carbon quaternary center, which were synthetically useful but challenging to construct, were obtained in up to 97% yield and 93% ee.

Graphical abstract: Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

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Article information

DOI
https://doi.org/10.1039/C1SC00295C
Article type
Edge Article
Submitted
16 May 2011
Accepted
20 Jun 2011
First published
07 Jul 2011

Chem. Sci., 2011,2, 1839-1841

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Enantioselective bromination/semipinacol rearrangement for the synthesis of β-bromoketones containing an all-α-carbon quaternary center

H. Li, F. Zhang, Y. Tu, Q. Zhang, Z. Chen, Z. Chen and J. Li, Chem. Sci., 2011, 2, 1839 DOI: 10.1039/C1SC00295C

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