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

被引：89

作者：

WIPF, P

MILLER, CP

VENKATRAMAN, S

FRITCH, PC

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 36期

关键词：

D O I：

10.1016/0040-4039(95)01322-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct oxazoline-->thiazoline conversion can be realized by thiolysis of oxazolines with H2S in methanol/triethylamine, followed by cyclodehydration with Burgess reagent. This protocol is high-yielding, chemoselective, and essentially free of racemization for C(5)-unsubstituted and trans-4,5-disubstituted peptide oxazolines. Thioamide intermediates are obtained regioselectively, thus the thiolysis of oxazolines offers an alternative to the thiation of peptides with Lawesson's reagent.

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页码：6395 / 6398

页数：4

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