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Asymmetric organocatalytic epoxidation of alpha,beta-unsaturated aldehydes with hydrogen peroxide
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2005 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 19, 6964-6965 p.Article in journal (Refereed) Published
Abstract [en]

The first asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes is presented. A chiral bisaryl−silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures of alcohols, and the scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities >94% ee. Furthermore, the direct synthesis of the sex pheromone from an acaric mite by asymmetric epoxidation of citral is presented.

Place, publisher, year, edition, pages
2005. Vol. 127, no 19, 6964-6965 p.
Keyword [en]
Asymmetric catalys, organocatalys, epoxdation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-14749DOI: 10.1021/ja051808sISI: 000229085200026Scopus ID: 2-s2.0-18744407280OAI: oai:DiVA.org:kth-14749DiVA: diva2:332790
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QC 20160601

Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2017-12-12Bibliographically approved

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Franzen, Johan.

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