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Communication | Regular issue | Vol 36, No. 9, 1993, pp.1965-1969
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6428
Stereocontrolled Formation of Functionalized erythro-1,2-Diols via Hydroboration of 2-Alkyl-4,5-dihydrofurans

Roger Amouroux,* Abdelmalik Slassi, and Christine Saluzzo

*Laboratoire de Chimie Organique Physique et Synthétique, Associe au CNRS, Université Claude Bernard, Lyon 1, 43, Bd du 11 Novembre 1918 69622 Villeurbanne Cedex, France

Abstract

trans-2-Alkyl-3-hydroxytetrahydrofurans, prepared by the stereospecific hydroboration / oxidation reaction of 2-alkyl-4,5-dihydrofurans, were regioselectively cleaved with (CH3)3SiCl/NaI to afford 1-iodo-erythro-3,4-diols in CH3CN or the corresponding acetonide derivatives in CH3COCH3.