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Gold(III)- and Platinum(II)-Catalyzed Domino Reaction Consisting of Heterocyclization and 1,2-Migration: Efficient Synthesis of Highly Substituted 3(2H)-Furanones

Stefan F. Kirsch, Jörg T. Binder, Clémence Liébert, Helge Menz

*Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany, Email: stefan.kirschch.tum.de

S. F. Kirsch, J. T. Binder, C. Liébert, H. Menz, Angew. Chem. Int. Ed., 2006, 45, 5878-5880.

DOI: 10.1002/anie.200601836 (free Supporting Information)


Abstract

A novel approach to 3(2H)-furanones combines a transition-metal-catalyzed activation of alkynes with a heterocyclization and subsequent 1,2-alkyl shift. Starting 2-hydroxy-2-alkynylcarbonyl compounds can be prepared by simple oxygenation of alkynyl carbonyl compounds using 2-iodoxybenzoic acid (IBX).


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IBX-Mediated α-Hydroxylation of α-Alkynyl Carbonyl Systems. A Convenient Method for the Synthesis of Tertiary Alcohols

S. F. Kirsch, J. Org. Chem., 2005, 70, 10210-10212.


Key Words

3(2H)-furanones, cylcopentanes, cyclization, domino reactions, heterocycles, platinum, rearrangement


ID: J06-Y2006-2810