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

被引：87
|
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.
引用
收藏
页码：6395 / 6398
页数：4
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