Synthesis of 4-Iodo-3-furanones Utilizing Electrophile-Induced Tandem Cyclization/1,2-Migration Reactions

Benedikt Crone and Stefan F. Kirsch*
Department Chemie, Technische Universitt Mnchen, Lichtenbergstrasse 4, D-85747 Garching, Germany stefan.kirsch@ch.tum.de
J. Org. Chem., 2007, 72 (14), pp 5435–5438
DOI: 10.1021/jo070695n
Publication Date (Web): June 8, 2007
Copyright © 2007 American Chemical Society
*

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

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Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in moderate to excellent yields.

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History

  • Published In Issue July 06, 2007
  • Received April 4, 2007

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