Issue 21, 2017
From the journal:

Chemical Communications

Chiral crotyl geminal bis(silane): a useful reagent for asymmetric Sakurai allylation by selective desilylation-enabled chirality transfer†

Zhiwen Chu,a   Kai Wang,a   Lu Gaoa  and  Zhenlei Song*ab  

* Corresponding authors

a Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, 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

Enantioselective synthesis of SiMe3/SiPh2Me-substituted crotyl geminal bis(silane) has been developed. This compound is a useful reagent for Ph3C+B(C6F5)4−-catalyzed asymmetric Sakurai allylation and one-pot Sakurai allylation/Prins cyclization processes. Chemoselective desilylation of SiPh2Me leads to efficient chirality transfer.

Graphical abstract: Chiral crotyl geminal bis(silane): a useful reagent for asymmetric Sakurai allylation by selective desilylation-enabled chirality transfer

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Article information

DOI
https://doi.org/10.1039/C7CC00632B
Article type
Communication
Submitted
23 Jan 2017
Accepted
22 Feb 2017
First published
22 Feb 2017

Chem. Commun., 2017,53, 3078-3081

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Chiral crotyl geminal bis(silane): a useful reagent for asymmetric Sakurai allylation by selective desilylation-enabled chirality transfer

Z. Chu, K. Wang, L. Gao and Z. Song, Chem. Commun., 2017, 53, 3078 DOI: 10.1039/C7CC00632B

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