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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

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Adam Bell, Dr Ross Harrington, Emeritus Professor Bill Clegg

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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) cyclohexaneform 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. © 2007 American Chemical Society.


Publication metadata

Author(s): Doherty S, Knight JG, Bell AL, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Organometallics

Year: 2007

Volume: 26

Issue: 9

Pages: 2465-2468

ISSN (print): 0276-7333

ISSN (electronic): 1520-6041

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/om070129i

DOI: 10.1021/om070129i


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