An Efficient Ir(III) Catalyst for the Asymmetric Transfer Hydrogenation of Ketones in Neat Water

Xiaohong Li; John Blacker; Ian Houson; Xiaofeng Wu; Jianliang Xiao

doi:10.1055/s-2006-932490

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Synlett 2006(8): 1155-1160
DOI: 10.1055/s-2006-932490

LETTER

An Efficient Ir(III) Catalyst for the Asymmetric Transfer Hydrogenation of Ketones in Neat Water

Xiaohong Li^a, John Blacker^b, Ian Houson^b, Xiaofeng Wu^a, Jianliang Xiao*^a
^a Liverpool Centre for Materials and Catalysis, Department of Chemistry, University of Liverpool, Liverpool L69 7ZD, UK
Fax: +44(151)7943589; e-Mail: j.xiao@liv.ac.uk;
^b NPIL Pharma, Leeds Road, Huddersfield, Yorkshire HD2 1GA, UK

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Publication History

Received 29 November 2005
Publication Date:
10 March 2006 (online)

Abstract
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Abstract

The chiral M-CsDPEN [M = Ru, Rh, Ir; CsDPEN = (R,R,R)- or (S,S,S)-N-camphorsulfonyl-1,2-diphenylethylenediamine] catalysts have been shown to be efficient for the asymmetric transfer hydrogenation (ATH) of aryl ketones by formate in neat water. Of particular note is the Ir-(R,R,R)-CsDPEN catalyst, which catalyzes the ATH of a wide range of ketones and delivers almost full conversions within a few hours at a S/C ratio of 1000 at 40 °C in most cases, with enantioselectivities up to 98% ee.

Key words

asymmetric transfer hydrogenation - ketones - water - formate - camphor ligand

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