P-Chirogenic ligand synthesis and catalysis

ORGN 778

Eoin F Clarke, eoin.clarke@ucd.ie1, Lee J Higham2, and Declan G Gilheany2. (1) Chemistry Department, University College Dublin, Belfield, Dublin 4, Ireland, (2) School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland
P-chirogenic ligands based upon the MOP architecture have been synthesised. An interesting crystal structure of an intermediate P-chirogenic oxide is illustrated. An expeditious route to the P-chiral phosphines which can by-pass the need for such phosphine oxide intermediates is shown. A number of racemic secondary phosphines have been prepared such as anisylphenyl, tert-butylphenyl and cyclohexylphenylphosphine. Their reactivity in nickel mediated couplings to binaphthyl backbones will be presented. The ligands have been used in asymmetric catalytic studies including arylboronic acid additions to aldehydes and the arylation of imines, and their efficacy is discussed.
 

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

Division of Organic Chemistry

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