One-Pot Copper(I)-Catalyzed Synthesis of 3,5-Disubstituted Isoxazoles

Trond V. Hansen,† Peng Wu, and Valery V. Fokin*
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037 fokin@scripps.edu
J. Org. Chem., 2005, 70 (19), pp 7761–7764
DOI: 10.1021/jo050163b
Publication Date (Web): August 13, 2005
Copyright © 2005 American Chemical Society
†

 On leave from The School of Pharmacy, University of Oslo, PO BOX 1155, N-0316 Blindern, Oslo, Norway.

,
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

3,5-Disubstituted isoxazoles are obtained in good yields by a convenient one-pot, three-step procedure utilizing a regioselective copper(I)-catalyzed cycloaddition reaction between in situ generated nitrile oxides and terminal acetylenes. Most functional groups do not interfere with the reaction, which can be performed in aqueous solvents without protection from oxygen. Since all reagents are used in stoichiometric amounts, formation of byproducts is minimized.

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History

  • Published In Issue September 16, 2005
  • Received January 26, 2005

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