THIOLYSIS OF OXAZOLINES - A NEW, SELECTIVE METHOD FOR THE DIRECT CONVERSION OF PEPTIDE OXAZOLINES INTO THIAZOLINES

Authors
WIPF P MILLER CP VENKATRAMAN S FRITCH PC
Citation
P. Wipf et al., THIOLYSIS OF OXAZOLINES - A NEW, SELECTIVE METHOD FOR THE DIRECT CONVERSION OF PEPTIDE OXAZOLINES INTO THIAZOLINES, Tetrahedron letters, 36(36), 1995, pp. 6395-6398
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
36
Year of publication
1995
Pages
6395 - 6398
Database
ISI
SICI code
0040-4039(1995)36:36<6395:TOO-AN>2.0.ZU;2-K
Abstract
A direct oxazoline-->thiazoline conversion can be realized by thiolysi s of oxazolines with H2S in methanol/triethylamine, followed by cyclod ehydration with Burgess reagent. This protocol is high-yielding, chemo selective, and essentially free of racemization for C(5)-unsubstituted and trans-4,5-disubstituted peptide oxazolines. Thioamide intermediat es are obtained regioselectively, thus the thiolysis of oxazolines off ers an alternative to the thiation of peptides with Lawesson's reagent .