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High-Atom Economic Approach To Prepare Chiral alpha-Sulfenylated Ketones
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: 0000-0001-8735-5397
Number of Authors: 42019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 17, p. 11219-11227Article in journal (Refereed) Published
Abstract [en]

Chiral alpha-sulfenylated ketones are versatile building blocks, although there are still several limitations with their preparation. Here we report a new two-step procedure, consisting of Pd-catalyzed hydrothiolation of propargylic alcohols followed by an enantioselective Rh isomerization of allylic alcohols. The isomerization reaction is the key step for obtaining the ketones in their enantioenriched form. The new methodology has a high atom economy and induces good to high levels of enantioselectivity; no waste is produced. A mechanism involving a Rh-hydride-enone intermediate is proposed for the isomerization reaction.

Place, publisher, year, edition, pages
2019. Vol. 84, no 17, p. 11219-11227
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-174868DOI: 10.1021/acs.joc.9b01424ISI: 000485089200066PubMedID: 31385499OAI: oai:DiVA.org:su-174868DiVA, id: diva2:1360753
Available from: 2019-10-14 Created: 2019-10-14 Last updated: 2019-10-14Bibliographically approved

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