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Allylation of aldehyde and imine substrates with in situ generated allylboronates - a simple route to enantioenriched homoallyl alcohols
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2005 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, 2539-2547 p.Article in journal (Refereed) Published
Abstract [en]

Allylation of aldehyde and imine substrates was achieved using easily available allylacetates and diboronate reagents in the presence of catalytic amounts of palladium. This operationally simple one-pot reaction has a broad synthetic scope, as many functionalities including, acetate, carbethoxy, amido and nitro groups are tolerated. The allylation reactions proceed with excellent regio- and stereoselectivity affording the branched allylic isomer. By employment of commercially available chiral diboronates enantioenriched homoallyl alcohols (up to 53% ee) could be obtained. The mechanistic studies revealed that the in situ generated allylboronates react directly with the aldehyde substrates, however the allylation of the sulfonylimine substrate requires palladium catalysis.

Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH & Co , 2005. no 12, 2539-2547 p.
Keyword [en]
Allylic compounds / Boron / Diboronates / Electrophilic addition / Homogenous catalysis / Palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-64958DOI: 10.1002/ejoc.200500069ISI: 000229947200012OAI: oai:DiVA.org:su-64958DiVA: diva2:460255
Funder
Swedish Research Council
Available from: 2013-01-30 Created: 2011-11-29 Last updated: 2017-12-08Bibliographically approved

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