Title: Thiolysis of oxazolines: A new, selective method for the direct conversion of peptide oxazolines into thiazolines
Abstract: 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.
Publication Year: 1995
Publication Date: 1995-09-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 96
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