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Diastereo- and Enantioselective Synthesis of Structurally Diverse Succinate, Butyrolactone, and Trifluoromethyl Derivatives by Iridium-Catalyzed Hydrogenation of Tetrasubstituted Olefins
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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2019 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 7, p. 6169-6176Article in journal (Refereed) Published
Abstract [en]

A highly efficient iridium N,P-ligand-catalyzed asymmetric hydrogenation of functionalized tetrasubstituted olefins lacking a directing group has been developed. Various structural diverse chiral succinate derivatives were obtained in high yields and excellent enantio- and diastereoselectivities (up to 99% ee) using 0.5-1.0 mol % catalyst loadings. This stereoselective reaction is applicable for the synthesis of chiral acyclic molecules (up to >99% ee) having two contiguous stereogenic centers and is compatible with various aromatic, aliphatic, and heterocyclic systems, a variety of functional groups of different electronic nature. Furthermore, this asymmetric protocol allows a short enantioselective route to the butyrolactone building block, an intermediate in the synthesis of anticancer agent BMS-871 and pharmaceuticals (2S)-(-)-Verapamil and (2S)-(-)-Gallopamil.

Place, publisher, year, edition, pages
2019. Vol. 9, no 7, p. 6169-6176
Keywords [en]
tetrasubstituted olefin, asymmetric hydrogenation, iridium catalysis, enantioselective, diastereoselective
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-171721DOI: 10.1021/acscatal.9b01508ISI: 000474812400037OAI: oai:DiVA.org:su-171721DiVA, id: diva2:1350411
Funder
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareKnut and Alice Wallenberg FoundationAvailable from: 2019-09-11 Created: 2019-09-11 Last updated: 2020-04-17Bibliographically approved

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Kerdphon, SutthichatPonra, SudiptaYang, JianpingWu, HaiboEriksson, LarsAndersson, Pher G.
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