Issue 48, 2010
From the journal:

Chemical Communications

The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes†

Yanzhao Wang,a   Biao Lua  and  Liming Zhang*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of California, Santa Barbara, USA
E-mail: zhang@chem.ucsb.edu
Fax: +1 805 893 4120

Abstract

A gold-catalyzed synthesis of 1-bromo/chloro-2-carboxy-1,3-dienes is developed using propargylic carboxylates containing halogenated alkynes as substrates. The reaction is highly diastereoselective, and the halogen atom at the alkyne terminus selectively promotes a 1,2-acyloxy migration. The diene products participate in the Diels–Alder and cross-coupling reactions.

Graphical abstract: The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes

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Article information

DOI
https://doi.org/10.1039/C0CC03669B
Article type
Communication
Submitted
05 Sep 2010
Accepted
03 Oct 2010
First published
29 Oct 2010

Chem. Commun., 2010,46, 9179-9181

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The use of Br/Cl to promote regioselective gold-catalyzed rearrangement of propargylic carboxylates: an efficient synthesis of (1Z, 3E)-1-bromo/chloro-2-carboxy-1,3-dienes

Y. Wang, B. Lu and L. Zhang, Chem. Commun., 2010, 46, 9179 DOI: 10.1039/C0CC03669B

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