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An Enantioselective Approach to the Preparation of Chiral Sulfones by Ir-Catalyzed Asymmetric Hydrogenation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry. (Joseph Samec)ORCID iD: 0000-0001-7779-1849
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2014 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 136, no 47, 16557-16562 p.Article in journal (Refereed) Published
Abstract [en]

Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2014. Vol. 136, no 47, 16557-16562 p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-236862DOI: 10.1021/ja5079877ISI: 000345720500016PubMedID: 25300238OAI: oai:DiVA.org:uu-236862DiVA: diva2:765722
Available from: 2014-11-24 Created: 2014-11-24 Last updated: 2017-12-05Bibliographically approved
In thesis
1. Noble Metal Catalysed Reductions and Rearrangements
Open this publication in new window or tab >>Noble Metal Catalysed Reductions and Rearrangements
2016 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The focus of this thesis has been organometallic catalysis applied to compounds containing heteroatoms which are usually poisonous to metal catalysts, by channelling their innate reactivity advantageously. The studies described in this thesis concentrate, in the first part, on iridium catalysed asymmetric hydrogenation (papers I and II) and in the second part, on gold catalysed internal rearrangements (papers III and IV). In each case, two classes of compounds are studied: pyridinium salts or sulphurous compounds. The asymmetric hydrogenation of pyridinium compounds was performed with 2% loading of N,P-ligated Ir catalyst with I2 additive (paper I) to achieve moderate to good enantiomeric excess (up to 98%). In paper II, olefinic sulphones were hydrogenated with an efficient 0.5% catalytic loading. In most cases full conversion was obtained and with good to excellent ees (up to 99%). The products of these reductions are chiral compounds, which could constitute further chemical building blocks. Palladium and gold were used sequentially in paper III, in order to perform a “Click” thiol-yne reaction followed by a semi-Pinacol rearrangement, leading to isolated yields of up to 98%. In paper IV The gold catalysed rearrangement of alkyl-pyridinium diynes was conducted, with a number of substrates providing >90% NMR yield. A highly selective hydrogenation was performed with a heterogeneous palladium catalyst to yield single diastereomer products. This methodology consists of up to three steps, with two catalysts in one pot.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2016. 63 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1337
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-272383 (URN)978-91-554-9453-7 (ISBN)
Public defence
2016-02-25, B/B21, BMC, Husargatan 3, Uppsala, 09:30 (English)
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Supervisors
Available from: 2016-02-03 Created: 2016-01-13 Last updated: 2016-02-12

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