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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.ORCID iD: 0000-0003-0223-1489
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-1012-5611
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-9620-8698
2011 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 2+3, p. 245-252Article 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, p. 245-252
Keywords [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, id: diva2:432160
Funder
Swedish Research CouncilAvailable from: 2011-08-01 Created: 2011-08-01 Last updated: 2020-02-20Bibliographically approved

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Santoro, StefanoHimo, FahmiCórdova, Armando
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