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Highly Diastereoselective Palladium-Catalyzed Oxidative Carbocyclization of Enallenes Assisted by a Weakly Coordinating Hydroxyl Group
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.ORCID iD: 0000-0001-8462-4176
Number of Authors: 32018 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 9, p. 3210-3214Article in journal (Refereed) Published
Abstract [en]

A highly diastereoselective palladium-catalyzed oxidative carbocyclization-borylation of enallenes assisted by a weakly coordinating hydroxyl group was developed. The reaction afforded functionalized cyclo-hexenol derivatives, in which the 1,3-relative stereo chemistry is controlled (d.r. > 50:1). Other weakly coordinating oxygen-containing groups (ketone, alkoxide, acetate) also assisted the carbocyclization toward cyclo-hexenes. The reaction proceeds via a ligand exchange on Pd of the weakly coordinating group with a distant olefin group. The high diastereoselectivity of the hydroxyl directed reaction could be rationalized by a face-selective coordination of the distant olefin. It was demonstrated that the primary coordination of the close-by oxygen containing functionality was necessary for the reaction to occur and removal of this functionality shut down the reaction.

Place, publisher, year, edition, pages
2018. Vol. 140, no 9, p. 3210-3214
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-156114DOI: 10.1021/jacs.7b13563ISI: 000427203600010PubMedID: 29425445OAI: oai:DiVA.org:su-156114DiVA, id: diva2:1204266
Available from: 2018-05-07 Created: 2018-05-07 Last updated: 2018-05-07Bibliographically approved

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Posevins, DanielsBäckvall, Jan-E.
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