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Communication | Special issue | Vol 72, No. 1, 2007, pp.115-122
Published online, 1st December, 2006
DOI: 10.3987/COM-06-S(K)13
Synthesis of Oxa-Bridged 7- and 8-Membered Rings via Indium-Mediated Annulation of 1,4- and 1,5-Dicarbonyl Compounds with 3-Iodo-2-[(trimethylsilyl)methyl]propene

Amir Allatabakhsh, Minh Pham, and Thomas Minehan*

*Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff St., Northridge, CA 91330, U.S.A.

Abstract

A variety of 1,4- and 1,5-dicarbonyl compounds undergo reaction with 3-iodo-2-[(trimethylsilyl)methyl]propene in the presence of indium metal in aqueous media to produce oxa-bridged 7- and 8-membered rings in good yields. The reaction mechanism likely involves intermolecular indium allylation of one carbonyl of the substrate, followed by indium-halide promoted intramolecular allylsilane cyclization. This procedure offers an environmentally friendly alternative to the analogous tin-mediated annulation process.