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

Benedikt Crone and Stefan F. Kirsch*

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

B. Crone, S. F. Kirsch, J. Org. Chem., 2007, 72, 5435-5438.

DOI: 10.1021/jo070695n

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Abstract

A sequence consisting of an electrophilic cyclization in the presence of N-iodosuccinimide (NIS) and an 1,2-migration allows the construction of 4-iodo-3-furanones from 2-alkynyl-2-silyloxy carbonyl compounds. In a more versatile variant, AuCl₃ catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in good yields.

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Key Words

Furanones, N-iodosuccinimide (NIS)

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ID: J42-Y2007-2250