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Enantioselective Conjugate Silyl Additions to alpha,beta-Unsaturated Aldehydes Catalyzed by Combination of Transition Metal and Chiral Amine Catalysts
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
Stockholm Univ, Dept Organ Chem, Arrhenius Lab, SE-10691 Stockholm, Sweden.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences, Engineering and Mathematics.
2011 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 2-3, 245-252 p.Article in journal (Refereed) Published
Abstract [en]

We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to alpha,beta-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding beta-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction can also generate a quaternary stereocenter with good enantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.

Place, publisher, year, edition, pages
2011. Vol. 353, no 2-3, 245-252 p.
Keyword [en]
asymmetric catalysis; organocatalysis; beta-silyl aldehydes; transition metal catalysis; alpha, beta-unsaturated aldehydes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-13474DOI: 10.1002/adsc.201000908ISI: 000287669600006Scopus ID: 2-s2.0-79951825587OAI: oai:DiVA.org:miun-13474DiVA: diva2:408772
Available from: 2011-04-06 Created: 2011-04-06 Last updated: 2011-12-16Bibliographically approved

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