Aminolysis of Resin-Bound N-Nosylaziridine-2-carboxylic Acids

Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesu...

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Bibliographic Details
Published in:Organic letters 2006-07, Vol.8 (15), p.3371-3374
Main Authors: Olsen, Christian A, Christensen, Caspar, Nielsen, Birgitte, Farah, Mohamed M, Witt, Matthias, Clausen, Rasmus P, Kristensen, Jesper L, Franzyk, Henrik, Jaroszewski, Jerzy W
Format: Article
Language:English
Subjects:
Amino Alcohols - chemistry
Aziridines - chemistry
Carboxylic Acids - chemistry
Heterocyclic Compounds - chemical synthesis
Molecular Structure
Stereoisomerism
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Summary:Solid-phase synthesis is a rapidly developing area of organic chemistry, of particular importance for medicinal chemistry and chemical biology. Aziridines have previously only rarely been applied in solid-phase synthesis. In the present work, aminolysis of resin-bound, spring-loaded N-nitrobenzenesulfonyl-activated aziridine-2-carboxylic acids has been optimized and employed in the synthesis of a number of open-chain and heterocyclic scaffolds, including enantiopure products.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol061304e