Aminolysis of resin-bound N-nosylaziridine-2-carboxylic acids.
[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.
Olsen
Christian A
CA
Department of Medicinal Chemistry, The Danish University of Pharmaceutical Sciences, DK-2100 Copenhagen, Denmark. cao@dfuni.dk
Christensen
Caspar
C
Nielsen
Birgitte
B
Farah
Mohamed M
MM
Mohamed
Farah M
FM
Witt
Matthias
M
Clausen
Rasmus P
RP
Kristensen
Jesper L
JL
Franzyk
Henrik
H
Jaroszewski
Jerzy W
JW
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
D000605:Amino Alcohols; D001388:Aziridines; D002264:Carboxylic Acids; D006571:Heterocyclic Compounds