(DIETHYLAMINO)SULFUR TRIFLUORIDE (DAST) AS A USEFUL REAGENT FOR THE PREPARATION OF 2-OXAZOLINES FROM 1,2-AMIDO ALCOHOLS

Authors
LAFARGUE P GUENOT P LELLOUCHE JP
Citation
P. Lafargue et al., (DIETHYLAMINO)SULFUR TRIFLUORIDE (DAST) AS A USEFUL REAGENT FOR THE PREPARATION OF 2-OXAZOLINES FROM 1,2-AMIDO ALCOHOLS, Heterocycles, 41(5), 1995, pp. 947-958
Citations number
52
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
41
Issue
5
Year of publication
1995
Pages
947 - 958
Database
ISI
SICI code
0385-5414(1995)41:5<947:(T(AAU>2.0.ZU;2-R
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 degrees C, a rapid (< 1 h) and stereoselective amide cyclization is observed without formation of acylaziridine by-pr oducts. The scope of this cyclization is discussed.