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Enantio- and Regioselective Ir-Catalyzed Hydrogenation of Di- and Trisubstituted Cycloalkenes
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.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 8
2016 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 36, 11930-11935 p.Article in journal (Refereed) Published
Abstract [en]

A number of cyclic olefins Were prepared and evaluated for the asymmetric hydrogenation reaction using novel N,P-ligated iridium imidazote-based Catalysts (Crabtree type). The diversity of these cyclic olefins spanned those having little functionality to others bearing strongly coordinating substituents and heterocycles. Excellent enantioselectivities were observed both for substrates having little functionality (up to >99% ee) and for substrates possessing functional groups several carbons away from the olefin. Substrates having functionalities such as carboxyl groups, alcohols, or heterocycles in the vicinity of the C=C bond were hydrogenated in high enantiomeric excess (up to >99% ee). The hydrogenation was also found to be regioselective, and by controlling the reaction conditions, selective hydrogenation of one of two trisubstituted olefins can be achieved: Furthermore, trisubstituted olefins can be selectively hydrogenated in the presence of tetrasubstituted olefins.

Place, publisher, year, edition, pages
2016. Vol. 138, no 36, 11930-11935 p.
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Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-135188DOI: 10.1021/jacs.6b07291ISI: 000383410700067PubMedID: 27548029OAI: oai:DiVA.org:su-135188DiVA: diva2:1048614
Available from: 2016-11-21 Created: 2016-11-01 Last updated: 2016-11-21Bibliographically approved

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Peters, Byron K.Liu, JianguoMargarita, CristianaRabten, WangchukKerdphon, SutthichatAndersson, Pher G.
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