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Synthesis of dehydroamino acids and didehydrodioxopiperazines and their conversion into α-mercapto-α-amino acid derivatives

✍ Scribed by Jacobus D. M. Herscheid; Henk P. H. Scholten; Marian W. Tijhuis; Harry C. J. Ottenheijm

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 600 KB
Volume: 100
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19811000208

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✦ Synopsis

Abstract

A synthesis of α,β‐dehydroamino acid derivatives 12 is described, which is of possible general applicability and might be useful for the preparation of peptides which have such a moiety in their sequence. In addition, several didehydrodioxopiperazines (13–17) have been prepared. The reactivity of these compounds towards liquid H~2~S in the presence of ZnCl~2~ has been studied. Only the dehydroalanine derivatives 12a and 13 gave α‐addition products; all other dehydroamino acid derivatives and cyclic dipeptides failed to react cleanly.

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