Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution

A detailed study is disclosed on the Rh‐mediated hydrogenative kinetic resolution of α,β‐unsaturated sulfoxides with alkyl and aryl substituents at the α‐, E‐ and Z‐positions of the double bond. This stereoselective catalytic methodology has enabled the preparation of highly enantioenriched (or even...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-08, Vol.2020 (28), p.4331-4338
Main Authors: Fernández‐Pérez, Héctor, Lao, Joan R., Grabulosa, Arnald, Vidal‐Ferran, Anton
Format: Article
Language:English
Subjects:
Alkenes
Aromatic compounds
Asymmetric catalysis
Hydrogenation
Kinetic resolution
Optical activity
Rhodium
Stereoselectivity
Substrates
Sulfoxides
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Summary:A detailed study is disclosed on the Rh‐mediated hydrogenative kinetic resolution of α,β‐unsaturated sulfoxides with alkyl and aryl substituents at the α‐, E‐ and Z‐positions of the double bond. This stereoselective catalytic methodology has enabled the preparation of highly enantioenriched (or even enantiopure) alkyl and aryl‐substituted (un)saturated sulfoxides via a simple and efficient synthetic operation. Moreover, the application of the hydrogenative KR to the preparation of valuable optically active sulfoxide‐containing building blocks or biologically active intermediates is described. The ability of a rhodium catalyst derived from phosphine‐phosphite ligands to hydrogenatively resolve a set of structurally diverse α,β‐unsaturated vinyl sulfoxides is reported. The practicality of the methodology was applied to the preparation of precursors of biologically active compounds.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202000592