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Synthesis and application of novel imidazole and 1H-tetrazolic acid containing catalysts in enantioselective organocatalyzed Diels-Alder reactions
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
2009 (English)In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 20, no 16, 1871-1876 p.Article in journal (Refereed) Published
Abstract [en]

Herein we report studies on the organocatalytic Diels-Alder reaction using a variety of catalysts capable of activating alpha,beta-unsaturated carbonyl compounds for reactions with dienes. The structurally attractive catalysts 4 and 14 were utilized in the enantioselective organocatalytic Diels-Alder reactions. Catalyst 4 provided the products in fair yields and more importantly in good enantioselectivities of up to 83% ee. Catalyst 14 was synthesized in high yield and was assessed in the enantioselective organocatalytic Diels-Alder reaction. Catalyst 14 proved to be a highly active and selective catalyst providing the products in high yield and high enantioselectivities up to 95% ee. (C) 2009 Elsevier Ltd. All rights reserved.

Place, publisher, year, edition, pages
2009. Vol. 20, no 16, 1871-1876 p.
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Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-127470DOI: 10.1016/j.tetasy.2009.07.029ISI: 000270625300007OAI: oai:DiVA.org:uu-127470DiVA: diva2:330234
Available from: 2010-07-15 Created: 2010-07-13 Last updated: 2017-12-12Bibliographically approved

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