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Paper | Regular issue | Vol 41, No. 5, 1995, pp.947-958
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6987
(Diethylamino)sulfur Trifluoride (DAST) as a Useful Reagent for the Preparation of 2-Oxazolines from 1,2-Amido Alcohols

Pierre Lafargue, Pierre Guenot, and Jean-Paul Lellouche*

*CEA, CE-Saclay, Départment de Biologie Cellulaire et Moléculaire, Service des Molécules Marquées, Bt 547, F-91191 Gif-sur-Yvette Cedex, France

Abstract

Acyclic 1,2-amido alcohols (6) react efficiently with a slight excess of (diethylamino)sulfur trifluoride (DAST) to afford the corresponding 2-oxazolines (10) in good yields ranging between 57-95%. Even at the low temperature of -78°C, a rapid (<1 h) and stereoselective amide cyclization is observed without formation of acylaziridine by-products. The scope of this cyclization is discussed.