Issue 53, 2015
From the journal:

Chemical Communications

Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes†

H. Yoshida,*ab   A. Shinke,a   Y. Kawanoa  and  K. Takakia  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Engineering, Hiroshima University, Higashi-Hiroshima 739-8527, Japan
E-mail: yhiroto@hiroshima-u.ac.jp
Fax: +81-82-424-5494
Tel: +81-82-424-7724

b ACT-C, Japan Science and Technology Agency, Higashi-Hiroshima 739-8527, Japan

Abstract

A variety of branched alkenylstannanes can directly be synthesized with excellent α-selectivity by the copper-catalyzed hydrostannylation using a distannane or a silylstannane, irrespective of the electronic and steric characteristics of terminal alkynes employed. Synthetic utility of the resulting branched alkenylstannane has been demonstrated by the total synthesis of bexarotene.

Graphical abstract: Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes

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Article information

DOI
https://doi.org/10.1039/C5CC02720A
Article type
Communication
Submitted
01 Apr 2015
Accepted
24 Apr 2015
First published
27 Apr 2015
This article is Open Access
Creative Commons BY license

Chem. Commun., 2015,51, 10616-10619

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Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes

H. Yoshida, A. Shinke, Y. Kawano and K. Takaki, Chem. Commun., 2015, 51, 10616 DOI: 10.1039/C5CC02720A

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