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Organocatalysts Promote Enantioselective 1,3-Dipolar Cycloadditions of Nitrones with 1-Cycloalkene-1-carboxaldehydes
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2003 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2003, no 15, p. 2782-2791Article in journal (Refereed) Published
Abstract [en]

In the presence of enantiopure organocatalysts, 1-cycloalkene-1-carboxaldehydes and various nitrones furnished fused isoxazolidines. Thus, some chiral pyrrolidinium salts catalyzed the formation of such cycloadducts in high diastereo- and enantioselectivity (up to 92% ee). The predominant diastereomer, the exo one, was mostly obtained in excellent diastereoselectivity (> 99:1 dr). Furthermore, after recrystallization of one of the cycloadducts, this was obtained enantiomerically pure (> 99% ee). The absolute configuration of one of the cycloadducts was determined. 

Place, publisher, year, edition, pages
2003. Vol. 2003, no 15, p. 2782-2791
Keywords [en]
dipolar cycloadditions
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-1583DOI: 10.1002/ejoc.200300172ISI: 000184500800007Scopus ID: 2-s2.0-0043157645Local ID: 801OAI: oai:DiVA.org:miun-1583DiVA, id: diva2:26615
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2017-12-13Bibliographically approved

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Karlsson, StaffanHögberg, Hans-Erik

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