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Synthesis of Dipeptides Containing Novel Cyclopropyl- and Cyclopropenyl-Substituted β- and γ-Amino Acids

✍ Scribed by Paulini, Klaus ;Reißig, Hans-Ulrich

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 567 KB
Volume: 1994
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199419940604

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✦ Synopsis

Abstract

The N‐silylated methyl 2‐aminocyclopropanecarboxylate 1 can be incorporated into a dipeptide via a CsF‐mediated condensation reaction with N‐tosylated phenylalanine chloride 5. Due to its instability the corresponding free β‐amino acid 4 could not be isolated up to now, and peptides containing this structural element have previously not been accessible. After desilylation, the aminomethyl‐substituted cyclopropane or cyclopropene derivatives trans‐ 10, 12, and 13 also provided N‐protected dipeptides in good yields. magnified image

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