ORGN 601 |
Novel sulfinyl imine ligands for asymmetric catalysis
| Jonathan A. Ellman and Laurie B. Schenkel. Department of Chemistry, University of California at Berkeley, Berkeley, CA 94720-1460 |
A novel class of P,N - sulfinyl imine ligands, which incorporates chirality solely about sulfur, has been developed. The ease with which sulfinyl imines can be prepared has enabled us to evaluate ligands incorporating a number of sterically and electronically diverse sulfinamide and phosphine moieties. Palladium complexes of these ligands catalyze the allylic alkylation reaction with high conversion and selectivity (>90% ee). Furthermore, the first reported X-ray crystal structure of a Pd-bound sulfinyl imine provides insight into binding mode and origins of stereoselectivity. The utility of P,N – sulfinyl imine ligands is further demonstrated in the Ir-catalyzed asymmetric hydrogenation of unfunctionalized olefins, in which high selectivity (>90% ee) has been achieved. |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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