Issue 79, 2013
From the journal:

Chemical Communications

[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)†

Lu Gao,a   Ji Lu,a   Zhenlei Song,*ab   Xinglong Lin,a   Yongjin Xua  and  Zhiping Yina  

* Corresponding authors

a Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu, China
E-mail: zhenleisong@scu.edu.cn

b State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu, China

Abstract

An unusual [1,5]-Brook rearrangement of the lithium alkoxide of geminal bis(silyl) homoallylic alcohol is described. The unique steric and electronic effects of geminal bis(silane) were found to be crucial for promoting this long-range silyl migration, as well as for facilitating the subsequent γ/Z-selective addition of silyl allyllithium with carbonyl compounds to synthesize diverse configurationally defined Z-vinylsilanes.

Graphical abstract: [1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)

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Article information

DOI
https://doi.org/10.1039/C3CC45002C
Article type
Communication
Submitted
04 Jul 2013
Accepted
31 Jul 2013
First published
01 Aug 2013

Chem. Commun., 2013,49, 8961-8963

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[1,5]-Brook rearrangement: an overlooked but valuable silyl migration to synthesize configurationally defined vinylsilane. The unique steric and electronic effects of geminal bis(silane)

L. Gao, J. Lu, Z. Song, X. Lin, Y. Xu and Z. Yin, Chem. Commun., 2013, 49, 8961 DOI: 10.1039/C3CC45002C

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