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Issue 3, 2013
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Platinum-catalyzed cyclizations viacarbene intermediates: syntheses of complementary positional isomers of isoxazoles

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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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Supplementary files

Article information


Submitted
04 Oct 2012
Accepted
05 Dec 2012
First published
10 Dec 2012

Chem. Sci., 2013,4, 1053-1058
Article type
Edge Article

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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