Issue 45, 2019
From the journal:

RSC Advances

Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon†

Ya Wu,a   Hua Chen,b   Wenyu Yang,b   Yu Fan,b   Lu Gao,*b   Zhishan Su, ORCID logo c   Changwei Hu ORCID logo c  and  Zhenlei Song ORCID logo *b  

* Corresponding authors

a Department of Biological and Chemical Engineering, Chongqing University of Education, Chongqing 400067, China

b Sichuan Engineering Laboratory for Plant-Sourced Drug, Research Center for Drug Industrial Technology, Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of Pharmacy, Sichuan University, Chengdu, China
E-mail: lugao@scu.edu.cn, zhenleisong@scu.edu.cn

c Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, China

Abstract

An asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes has been developed via Si-to-C chirality transfer. Mechanistic studies reveal that the silyl group migrates with retention of configuration. The stereochemical outcome of the newly formed stereogenic carbon center, which has remained a longstanding question, is also clarified, suggesting a diastereoselective Si to C chirality transfer without loss of enantiomeric excess.

Graphical abstract: Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon

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Article information

DOI
https://doi.org/10.1039/C9RA05482K
Article type
Paper
Submitted
17 Jul 2019
Accepted
09 Aug 2019
First published
21 Aug 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 26209-26213

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Asymmetric retro-[1,4]-Brook rearrangement of 3-silyl allyloxysilanes via chirality transfer from silicon to carbon

Y. Wu, H. Chen, W. Yang, Y. Fan, L. Gao, Z. Su, C. Hu and Z. Song, RSC Adv., 2019, 9, 26209 DOI: 10.1039/C9RA05482K

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