(Diethylamino)sulfur trifluoride (DAST) as a useful reagent for the preparation of 2-oxazolines from 1,2-amido alcohols

Pierre Lafargue, Pierre Guenot, Jean Paul Lellouche

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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.

Original languageEnglish
Pages (from-to)947-958
Number of pages12
JournalHeterocycles
Volume41
Issue number5
DOIs
StatePublished - 1 May 1995
Externally publishedYes

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