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Synfacts 2006(2): 0111-0111  
DOI: 10.1055/s-2005-924825
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Concept for the Regioselective Synthesis of 1,2,3-Triazoles

Contributor(s): Victor Snieckus, Robert Engqvist
A. K. Feldman, B. Colasson, K. B. Sharpless*, V. V. Fokin*
The Scripps Research Institute, La Jolla, USA
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

The regioselective capture of the less substituted isomers of allylic azides via a copper(I)-catalyzed cycloaddition with phenylacetylene to form 1,2,3-triazoles is reported. This ingenious method depends upon the shift of the dynamic [3.3]-sigmatropic equilibrium of the allylic azides via the irreversible nature of the [2+3] cycloaddition process. Although not yet sufficiently explored in terms of scope, the synthesis provides products in good to excellent yields.