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Enantioselective conjugate silyl additions to α,β-unsaturated aldehydes catalyzed by combination of transition metal and chiral amine catalysts
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.
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 α,β-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding β-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 canalso generate a quaternary stereocenter with goodenantioselectivity. 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, bsilyl aldehydes, transition metal catalysis, α, β-unsaturated aldehydes
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-59924DOI: 10.1002/adsc.201000908ISI: 000287669600006OAI: oai:DiVA.org:su-59924DiVA: diva2:432160
Funder
Swedish Research Council
Available from: 2011-08-01 Created: 2011-08-01 Last updated: 2017-12-08Bibliographically approved

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