Issue 45, 2009
From the journal:

Chemical Communications

Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes†

Chung-Meng Chao,a   Denis Beltrami,a   Patrick Y. Toulleca  and  Véronique Michelet*a  

* Corresponding authors

a Laboratoire Charles Friedel, Ecole Nationale Supérieure de Chimie de Paris UMR 7223, 11 rue P. et M. Curie, F-75231 Paris Cedex 05, France
E-mail: veronique-michelet@chimie-paristech.fr

Abstract

The enantioselective asymmetric gold-catalyzed cycloisomerization reactions of heteroatom tethered 1,6-enynes are conducted in the presence of a chiral cationic Au(I) catalyst ((R)-4-MeO-3,5-(t-Bu)2-MeOBIPHEP-(AuCl)2/AgOTf system) in toluene under mild conditions and lead to functionalized bicyclo[4.1.0]heptene derivatives in excellent enantiomeric excesses ranging from 90–98%.

Graphical abstract: Asymmetric Au(i)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes

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Article information

DOI
https://doi.org/10.1039/B913554E
Article type
Communication
Submitted
07 Jul 2009
Accepted
29 Sep 2009
First published
14 Oct 2009

Chem. Commun., 2009, 6988-6990

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Asymmetric Au(I)-catalyzed synthesis of bicyclo[4.1.0]heptene derivatives via a cycloisomerization process of 1,6-enynes

C. Chao, D. Beltrami, P. Y. Toullec and V. Michelet, Chem. Commun., 2009, 6988 DOI: 10.1039/B913554E

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