Asymmetric catalysts for the hydrogenation of ketones

ORGN 790

Yingjian Xu, Yingjian.Xu@warwick.ac.uk1, Martin Wills, m.wills@warwick.ac.uk1, Gary Woodward2, and Gordon Docherty, Gordon.Docherty@eu.rhodia.com3. (1) Department of Chemistry, University of Warwick, Gibbit Hill Road, Coventry, CV4 7AL, United Kingdom, (2) Rhodia Inc, Bristol, PA 19007, (3) Phosphorus and Performance Derivatives, Rhodia Consumer Specialities Ltd, PO Box 80, Trinity Street, Oldbury, B69 4LN, United Kingdom
The combination of a diphosphine with a diamine within a ruthenium complex of type 1 below results in the formation of an excellent catalyst for the asymmetric hydrogenation of simple ketones to enantiomerically enriched alcohols. In this poster presentation, we shall report the results of our recent investigation into the synthesis of novel monodentate phosphorus ligands (i.e. Br-XuPHOS, S-8) for use in this application to ketone reduction. Using a process of statistical experimental design, we have been able to optimise the catalyst and the reaction conditions to point where high activities (S/C up to 10,000) and enantiomeric excesses (up to 99%) could be routinely obtained. Our ligands also benefit from a simple structure and ready availability from inexpensive precursors. See Xu, Y. J.; Alcock, N. W.; Clarkson, G. J.; Docherty, G.; Woodward, G.; Wills, M. Org. Lett .2004, 6, 4105-4107.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005