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Paper | Regular issue | Vol 31, No. 2, 1990, pp.233-240
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4896
Synthesis of (4’R)- and (4’S)-5-(2’,2’-Dimethyl-1’,3’-dioxolan-4’-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazoles and (4’R)-5-(2’,2’-Dimethyl-1’,3’-dioxolan-4’-yl)-3-phenyl-1,2,4-oxadiazole

Louis Cottier, René Faure, Gérard Descotes,* and Rajendrra Mohan Srivastava

*Laboratoire de Chimie Organique II, Université Lyon I, U. A. CNRS 463, 43 Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France

Abstract

Chiral 3,5-disubstituted 4,5-dihydro-1,2,4-oxadiazoles (3, 4) have been prepared starting from benzamidoxime (1) and (R)-(-)-2,3-O-isoproppylideneglyceraldehyde (2). The structure of 3 was establised as (4’R)-5-(2’,2’-dimethyl-1’,3’-dioxolan-4’-yl)-3-phenyl-4,5-dihydro-1,2,4-oxadiazole by X-ray diffrection analysis on a single crystal. Mild possassium permanganate oxidationof a mixture of 3 and 4 gave the corresponding 1,2,4-oxadiazole (5).