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Enantioselective organocatalytic conjugate addition of fluorocarbon nucleophiles to 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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2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 39, 10013-10017 p.Article in journal (Refereed) Published
Abstract [en]

A highly chemo- and enantioselective organocatalytic addition of fluorocarbon nucleophiles, such as 1-fluoro-bis(phenylsulfonyl)methane, toα,β-unsaturated aldehydes is presented (see scheme). The reactions are catalyzed by simple chiral amines and give access to optically active fluorine derivatives in good yields and up to 95 % ee. Notably, the methodology can be applied to the formation of a chiral quaternary carbon center bearing a fluorine atom with high enantioselectivity.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA , 2009. Vol. 15, no 39, 10013-10017 p.
Keyword [en]
aldehydes, asymmetric catalysis, chemoselectivity, fluorine, organocatalysis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-30471DOI: 10.1002/chem.200901260ISI: 000270854200010OAI: oai:DiVA.org:su-30471DiVA: diva2:272405
Available from: 2009-10-15 Created: 2009-10-15 Last updated: 2017-12-12Bibliographically approved

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Zhao, Gui-LingDeiana, LucaDziedzic, PawelHammar, PeterSun, JunliangCórdova, Armando
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Department of Organic ChemistryDepartment of Structural ChemistryDepartment of Physical, Inorganic and Structural Chemistry
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Chemistry - A European Journal
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