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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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School of Natural Sciences, Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, U.K.
Cite this: Organometallics 2007, 26, 9, 2465–2468
Publication Date (Web):March 24, 2007
https://doi.org/10.1021/om070129i
Copyright © 2007 American Chemical Society

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    Abstract

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    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.

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    Text and figures giving experimental procedures and characterization data for all compounds and GC analysis of the reduction products and a CIF file giving crystal data for compound 4. This material is available free of charge via the Internet at http://pubs.acs.org.

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    19. Simon Doherty, Julian G. Knight, Adam L. Bell, Ross W. Harrington, William Clegg. 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.. ChemInform 2007, 38 (35) https://doi.org/10.1002/chin.200735084

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