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High-Atom Economic Approach To Prepare Chiral alpha-Sulfenylated Ketones
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.ORCID-id: 0000-0001-8735-5397
Rekke forfattare: 42019 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, nr 17, s. 11219-11227Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2019. Vol. 84, nr 17, s. 11219-11227
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URN: urn:nbn:se:su:diva-174868DOI: 10.1021/acs.joc.9b01424ISI: 000485089200066PubMedID: 31385499OAI: oai:DiVA.org:su-174868DiVA, id: diva2:1360753
Tilgjengelig fra: 2019-10-14 Laget: 2019-10-14 Sist oppdatert: 2019-10-14bibliografisk kontrollert

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