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Allylation of aldehyde and imine substrates with in situ generated allylboronates - a simple route to enantioenriched homoallyl alcohols
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0002-9349-7137
2005 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 12, s. 2539-2547Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
Weinheim: Wiley-VCH Verlag GmbH & Co , 2005. nr 12, s. 2539-2547
Emneord [en]
Allylic compounds / Boron / Diboronates / Electrophilic addition / Homogenous catalysis / Palladium
HSV kategori
Forskningsprogram
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-64958DOI: 10.1002/ejoc.200500069ISI: 000229947200012OAI: oai:DiVA.org:su-64958DiVA, id: diva2:460255
Forskningsfinansiär
Swedish Research CouncilTilgjengelig fra: 2013-01-30 Laget: 2011-11-29 Sist oppdatert: 2019-12-16bibliografisk kontrollert

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