Header

UZH-Logo

Maintenance Infos

The Application of 3-Amino-2H-azirines as Amino Acid Equivalents


Heimgartner, Heinz (1986). The Application of 3-Amino-2H-azirines as Amino Acid Equivalents. Israel Journal of Chemistry, 27(1):3-15.

Abstract

3-amino-2H-azirines undergo a number of ring opening reactions. The cleavage of the azirine-N(1), C(3) double bond leads thereby to synthons which can be considered as amino acid equivalents. The reaction of 3-amino-2H-azirines with carboxylic acids yields N-acyl amino acid amides, which can be converted by a selective amide cleavage to the corresponding N-acyl amino acids. 2-Oxazolin-5-ones are intermediates of this amide cleavage. This reaction sequence has been used for the extension of peptide chains as well as for a number of heterocycle syntheses. Likewise, the described synthesis of cyclic depsipeptides and lactones by direct amide cyclization proceeds via 2-oxazolin-5-one intermediates. The selective amide cleavage was also applied to a novel method for the resolution of enantiomeric amino acid derivatives.

Abstract

3-amino-2H-azirines undergo a number of ring opening reactions. The cleavage of the azirine-N(1), C(3) double bond leads thereby to synthons which can be considered as amino acid equivalents. The reaction of 3-amino-2H-azirines with carboxylic acids yields N-acyl amino acid amides, which can be converted by a selective amide cleavage to the corresponding N-acyl amino acids. 2-Oxazolin-5-ones are intermediates of this amide cleavage. This reaction sequence has been used for the extension of peptide chains as well as for a number of heterocycle syntheses. Likewise, the described synthesis of cyclic depsipeptides and lactones by direct amide cyclization proceeds via 2-oxazolin-5-one intermediates. The selective amide cleavage was also applied to a novel method for the resolution of enantiomeric amino acid derivatives.

Statistics

Citations

16 citations in Web of Science®
6 citations in Scopus®
Google Scholar™

Altmetrics

Additional indexing

Item Type:Journal Article, refereed, further contribution
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:German
Date:1986
Deposited On:04 Jun 2014 08:29
Last Modified:05 Apr 2016 17:54
Publisher:Wiley-Blackwell
ISSN:0021-2148
Publisher DOI:https://doi.org/10.1002/ijch.198600002

Download

Full text not available from this repository.
View at publisher