The Simple Synthesis of Chiral Polyazaoxacoronands Derived from α-Amino Acids

Bisamidation of oxaloyl chloride using L-amino acid methyl ester hydrochlorides afforded chiral diesters. The following reactions of diesters with 2,2-(ethylene-dioxy)diethylamine, afforded tetramides possessing C 2 symmetry. Coupling of N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine wi...

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Published inSupramolecular chemistry Vol. 12; no. 1; pp. 93 - 95
Main Authors Achmatowicz, Michal, Szczepańska, Agnieszka, Gryko, Daniel T., Salański, Piotr, Jurczak, Janusz
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 01.09.2000
Subjects
high pressure
macrocyclization
polyazaoxacoronands
α-amino acids
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Summary:Bisamidation of oxaloyl chloride using L-amino acid methyl ester hydrochlorides afforded chiral diesters. The following reactions of diesters with 2,2-(ethylene-dioxy)diethylamine, afforded tetramides possessing C 2 symmetry. Coupling of N-hydroxysuccinimide ester of N-benzyloxycarbonyl-L-alanine with 1,5-diamino-3-oxapentane, followed by cleavage of protecting groups, afforded an optically active diamine, which was transformed consequently into tetramide via the reaction with diglycolic acid dimethyl ester under high pressure conditions.
ISSN:1061-0278
1029-0478
DOI:10.1080/10610270008029806