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Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers
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: 0000-0001-8431-6368
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-7928-1877
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2018 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 42, p. 13878-13883Article in journal (Refereed) Published
Abstract [en]

The synthesis of chiral fluorine containing motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation of readily available vinyl fluorides. Various aromatic, aliphatic, and heterocyclic systems with a variety of functional groups were found to be compatible with the reaction and provide the highly desirable product as single diastereomers with excellent enantioselectivities.

Place, publisher, year, edition, pages
2018. Vol. 140, no 42, p. 13878-13883
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-162908DOI: 10.1021/jacs.8b08778ISI: 000448755200052PubMedID: 30265529OAI: oai:DiVA.org:su-162908DiVA, id: diva2:1272642
Funder
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareKnut and Alice Wallenberg FoundationAvailable from: 2018-12-19 Created: 2018-12-19 Last updated: 2020-04-17Bibliographically approved

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