Novel ruthenium (II) catalysts for asymmetric transfer hydrogenation of ketones and imines in the synthesis of enantio-pure cyclic amines

ORGN 118

Fung Kei Cheung, F.K.Cheung@warwick.ac.uk1, Martin Wills, m.wills@warwick.ac.uk1, and Mark A. Graham, Mark.A.Graham@astrazeneca.com2. (1) Department of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, United Kingdom, (2) R&D Alderley Park, AstraZeneca, Alderley Park, Macclesfield, Cheshire, SK10 4TF, United Kingdom
The synthesis and applications of novel ruthenium (II) catalysts of general structure 1 is described.  In particular, the asymmetric reductions of tBoc-amino ketones 2 to give alcohols 3 have been studied.  Subsequent deprotection follow by intramolecular cyclisation will deliver asymmetric cyclic amines 4, precursors of many biologically active molecules.  An alternative approach is cyclisation of 2 to imines 5 followed by asymmetric reduction to 4.  This will also be described.  The methodology developed can be used to generate underpinning processes which may be employed for the synthesis of potential pharmaceutical products.

The steric and electronic effects resulting from the addition of various substitutents on the ruthenium arene ring will be reported.

 

Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006