Issue 3, 2013
From the journal:

Chemical Science

Platinum-catalyzed cyclizations viacarbene intermediates: syntheses of complementary positional isomers of isoxazoles†

Paul A. Allegrettia  and  Eric M. Ferreira*a  

* Corresponding authors

a Colorado State University, Department of Chemistry, Fort Collins, CO, USA
E-mail: emferr@mail.colostate.edu
Tel: +1-970-491-6379

Abstract

A novel synthesis of regioisomeric isoxazoles is described. Using catalytic platinum, both propargylic N-hydroxycarbamates and N-alkoxycarbonyl amino ethers can be cyclized to form differentially substituted isoxazoles. Reaction conditions are developed that address specific aspects of the catalytic manifold. A unique mechanism involving a Pt-carbene intermediate is proposed, and deuterium labeling studies corroborate this hypothesis. This regiocomplementary approach to isoxazoles is highlighted in the syntheses of antirhinovirus analogues, illustrating the relevance of this science to medicinal chemistry.

Graphical abstract: Platinum-catalyzed cyclizations via carbene intermediates: syntheses of complementary positional isomers of isoxazoles

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Article information

DOI
https://doi.org/10.1039/C2SC21671J
Article type
Edge Article
Submitted
04 Oct 2012
Accepted
05 Dec 2012
First published
10 Dec 2012

Chem. Sci., 2013,4, 1053-1058

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Platinum-catalyzed cyclizations via carbene intermediates: syntheses of complementary positional isomers of isoxazoles

P. A. Allegretti and E. M. Ferreira, Chem. Sci., 2013, 4, 1053 DOI: 10.1039/C2SC21671J

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