ORGN 774 |
| Recent work in our laboratory has shown that a new range of enantiopure cis-dihydrodiols, can be obtained from mono-and polycyclic- arenes and azaarenes by large-scale biotransformation methods, using selected bacterial mutant strains. containing different dioxygenase types. These cis-dihydrodiols can in turn be used in the synthesis of new enantiopure bipyridine and cis-amino-alcohol ligands. Herein we report the biotransformation of 2-chloro-substituted -quinoline, -phenylpyridine and -biphenyl substrates to their corresponding cis-dihydrodiols and their use as precursors in the synthesis of enantiopure C2-symmetric bipyridine, bipyridine-N,N-dioxide and cis-amino-alcohol ligands. These new chiral ligands have been tested in different asymmetric reactions including:-hydrogenation of ketones, allylic hydroxylation and cyclopropantion of alkenes. To date enantiomeric excess values in excess of 90% ee have been obtained in some cases. |
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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 |