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Communication | Special issue | Vol 79, No. 1, 2009, pp.353-358
Published online, 23rd October, 2008
DOI: 10.3987/COM-08-S(D)22
■ Stereoselective Synthesis of 5-Substituted 2-Allyl-3-oxotetrahydrofuran-2-carboxylates Using Rhodium(II)-Catalyzed Oxonium Ylide Formation–[2,3] Shift

Takayuki Yakura,* Katsuaki Matsui, Kazumasa Matsuzaka, and Masayuki Yamashita

*Faculty of Pharmaceutical Sciences, Graduate School, Toyama University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan

Abstract

Reaction of 5-allyloxy-2-diazo-3-ketoesters 1 with catalytic amount of dirhodium(II) tetraacetate in dichloromethane proceeded in high yields with excellent stereoselectivities to give methyl 5-substituted 2-allyl-3-oxotetrahydro- furan-2-carboxylates 2, which are suitable intermediates for synthesis of heliespirones and their derivatives.