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Sterically goverend selectivity in palladium-assisted allylic alkylation
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2011 (English)In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 30, 230-238 p.Article in journal (Refereed) Published
Abstract [en]

The selectivity in the Pd-assisted allylic alkylation has been investigated in a system with a ligand tethered to the allylic moiety. Isolation of (η3-allyl)Pd complexes and stoichiometric reaction with malonate nucleophiles allowed separation of various factors influencing the regioselectivity in a system that cannot undergo apparent rotation. Unexpectedly, trans effects were found to have only a minor influence on the selectivity, whereas changing the tether length could shift the preference from favored internal to dominant terminal attack. DFT-assisted analysis revealed that the dominant selectivity-determiningfactors are the forced rotation of the allylic moiety and an important steric repulsion from a syn-alkyl substituent

Place, publisher, year, edition, pages
2011. Vol. 30, 230-238 p.
National Category
Organic Chemistry
URN: urn:nbn:se:su:diva-70977DOI: 10.1021/om1007264OAI: diva2:483434
Swedish Research Council
Available from: 2012-01-25 Created: 2012-01-25 Last updated: 2012-01-25Bibliographically approved

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Åkermark, Björn
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Department of Organic Chemistry
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