N-THIOACYLATION OF BETA-AMINO ALCOHOLS BY N-(THIOACYL)PHTHALIMIDES - A FACILE SYNTHESIS OF ALPHA-AMINO-ACID THIAZOLINES

Authors
BRAIN CT HALLETT A KO SY
Citation
Ct. Brain et al., N-THIOACYLATION OF BETA-AMINO ALCOHOLS BY N-(THIOACYL)PHTHALIMIDES - A FACILE SYNTHESIS OF ALPHA-AMINO-ACID THIAZOLINES, Tetrahedron letters, 39(1-2), 1998, pp. 127-130
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
1-2
Year of publication
1998
Pages
127 - 130
Database
ISI
SICI code
0040-4039(1998)39:1-2<127:NOBABN>2.0.ZU;2-I
Abstract
beta-amino alcohols are selectively N-thioacylated by N-(thioacyl)phth alimides under very mild conditions to provide N-(hydroxyethyl)thioami des in high yields. Cyclodehydration with Burgess reagent then provide s alpha-amino acid thiazolines. This approach provides a convenient al ternative to those based upon thionation of a preformed N-(hydroxyethy l)amide. (C) 1997 Elsevier Science Ltd. All rights reserved.