Asymmetric Transfer Hydrogenation of 1,3-Alkoxy/Aryloxy Propanones Using Tethered Arene/Ru(II)/TsDPEN Complexes

A series of propanones containing combinations of aryloxy and alkoxy substituents at the 1- and 3-positions were reduced to the alcohols via asymmetric transfer hydrogenation using a tethered Ru­(II)/TsDPEN catalyst. The enantioselectivities of the reductions reveal a complex pattern of electronic a...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 11; pp. 2789 - 2792
Main Authors Forshaw, Sam, Matthews, Alexander J, Brown, Thomas J, Diorazio, Louis J, Williams, Luke, Wills, Martin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
LIGAND BIFUNCTIONAL CATALYSIS
KETONES
ENANTIOSELECTIVE SYNTHESIS
DIASTEREOSELECTIVE SYNTHESIS
REDUCTION
MECHANISM
CARBONYL-COMPOUNDS
RUTHENIUM CATALYSTS
ALCOHOL)-CATALYZED TRANSFER HYDROGENATION
DYNAMIC KINETIC RESOLUTION
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Summary:A series of propanones containing combinations of aryloxy and alkoxy substituents at the 1- and 3-positions were reduced to the alcohols via asymmetric transfer hydrogenation using a tethered Ru­(II)/TsDPEN catalyst. The enantioselectivities of the reductions reveal a complex pattern of electronic and steric effects which, when used in a matched combination, can lead to the formation of products of up to 68% ee (84:16 er) from this highly challenging class of substrate.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00756