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Note | Regular issue | Vol 55, No. 7, 2001, pp.1323-1328
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9210
Convenient New Syntheses of R-(+)-5-Benzyloxymethyl-5H-furan-2-one. A Building Block en route to L-Nucleosides

Fabio Fazio, Davis Maliakal, and Manfred P. Schneider*

*FB-9, Organische Chemie, Bergische Universität - Gesamthochschule Wuppertal, Gaußstraße 20, 42097 Wuppertal, Germany

Abstract

R-(+)-5-Benzyloxymethyl-5H-furan-2-one (R-(1)) was obtained from commercially available R-(-)-2-benzyloxymethyl oxirane (R-(2)) in two and three steps, respectively. Key steps are a) the nucleophilic ring opening of the oxirane moiety with dianions derived from either PhSeCH2CO2H or PhSCH2CO2H; b) oxidation to the corresponding 1-oxides and c) concomitant or thermally induced syn-elimination. R-(1) was obtained with >97% ee and >95% ee, respectively.