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Catalytic asymmetric aziridination of α, β- unsaturated aldehydes
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2011 (English)In: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011, American Chemical Society , 2011Conference paper, Published paper (Other academic)
Abstract [en]

The development, scope and application of the highly enantioselective organocatalytic aziridination of a, b- unsaturated aldehydes is presented. The aminocatalytic aziridination of a, b- unsaturated aldehydes enables the asymmetric formation of b-formylaziridines with up to >19:1 dr and 99% ee. The aminocatalytic aziridination of a-monosobstituted enals gives access to terminal a-substituted-a-formyl aziridines in high yields and up to 99% ee. In the case of the organocatalytic aziridination of disubstituted a, b-unsaturated aldehydes, the transformations gives nearly enantiomeric pure b-formyl-functionalized aziridine products. A higly enantioselective one-pot cascade sequence based on combination of asymmetric amine and N-heterocyclic carbene catalysis is also disclosed. This transformation gives the corresponding N-Boc and N-Cbz protected b-amino acid esters with ee´s ranging from 92-99%.

Place, publisher, year, edition, pages
American Chemical Society , 2011.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-62001OAI: oai:DiVA.org:su-62001DiVA: diva2:439331
Available from: 2011-09-07 Created: 2011-09-07Bibliographically approved

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Deiana, LucaCórdova, ArmandoZhao, Gui-LingSun, Junliang
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