Asymmetric hydrogenation of ketones with ruthenium complexes of rac- and enantiopure (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane: A comparative study with rac- and (R)-BINAP

doi:10.1021/OM070129I

Paper

Asymmetric hydrogenation of ketones with ruthenium complexes of rac- and enantiopure (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane: A comparative study with rac- and (R)-BINAP

Published Mar 24, 2007 · S. Doherty, J. Knight, Adam L. Bell

Organometallics

Q1 SJR score

12

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0

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Abstract

Ruthenium(II) complexes of the type trans-[RuCl2{1,2-bis((diphenylphosphino)methyl)cyclohexane}(diamine)] based on the inexpensive and easy-to-prepare rac- and (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane form highly active and enantioselective catalysts for the asymmetric hydrogenation of a wide range of aryl and heteroaryl ketones, in most cases giving ee's that exceed those obtained with their BINAP counterparts. Although precatalysts based on 1,2-bis((diphenylphosphino)methyl)cyclohexane slowly isomerize in solution to afford the thermodynamically favored isomer with a cis arrangement of chlorides, catalysts generated from both isomers afford similar enantioselectivities.

Study Snapshot

Ruthenium complexes based on rac- and (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane provide highly active and enantioselective catalysts for asymmetric hydrogenation of aryl and heteroaryl keto

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Asymmetric hydrogenation of ketones with ruthenium complexes of rac- and enantiopure (S,S)-1,2-bis((diphenylphosphino)methyl)cyclohexane: A comparative study with rac- and (R)-BINAP

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References

Citations

Biaryl diphosphine ligands and their ruthenium complexes: Preparation and use for catalytic hydrogenation of ketones

Biaryl diphosphine ligands and their ruthenium complexes can catalyze the hydrogenation of ketones, resulting in chiral alcohols with enantioselectivity up to 93%.

Tribenzotriquinacene receptors for C60 fullerene rotors: towards C3 symmetrical chiral stators for unidirectionally operating nanoratchets.

The synthesized tribenzotriquinacene receptor (7) shows potential as a chiral stator in unidirectionally operating nanoratchets due to its C3 point group symmetry and stability constants.

C–H Activation at a Ruthenium(II) Complex – The Key Step for a Base‐Free Catalytic Transfer Hydrogenation?

C-H bond cleavage at the pyrimidine ring is crucial for activation of air-stable, phosphane-free transfer-hydrogenation catalysts without external bases.

New dinuclear ruthenium complexes: structure and oxidative catalysis.

New dinuclear ruthenium complexes show promising oxidative catalysis and epoxidation activity, with complex 3(2+) showing excellent performance for cis--methylstyrene oxide generation.

“In situ” Activation of Racemic RuII Complexes: Separation of trans and cis Species and Their Application in Asymmetric Reduction

Racemic RuII complexes with chiral DPEN can efficiently separate optically pure complexes in cis and trans arrangements, making them useful for asymmetric hydrogenation of ketones.