title: Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids.
abstract: [Structure: see text] 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.
authors.affiliation: Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, DK-2100 Copenhagen, Denmark. cao@dfuni.dk
authors.forename: Christian A
authors.initials: CA
authors.lastname: Olsen
authors.forename: Caspar
authors.initials: C
authors.lastname: Christensen
authors.forename: Birgitte
authors.initials: B
authors.lastname: Nielsen
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Farah
authors.forename: Farah M
authors.initials: FM
authors.lastname: Mohamed
authors.forename: Matthias
authors.initials: M
authors.lastname: Witt
authors.forename: Rasmus P
authors.initials: RP
authors.lastname: Clausen
authors.forename: Jesper L
authors.initials: JL
authors.lastname: Kristensen
authors.forename: Henrik
authors.initials: H
authors.lastname: Franzyk
authors.forename: Jerzy W
authors.initials: JW
authors.lastname: Jaroszewski
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry; D001388:Aziridines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000605:Amino Alcohols; D001388:Aziridines; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds