Understanding selective yet general chiral catalysts

ORGN 228

Eric N. Jacobsen, jacobsen@chemistry.harvard.edu, Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138
Small molecule catalysts can be general (by accepting a broad range of substrates), and yet selective (by inducing high kinetic control in reactions on those substrates). This apparent paradox is manifested in many ways in asymmetric catalysis. For example, certain chiral ligand frameworks are useful for an extraordinarily wide range of mechanistically unrelated reactions. These “privileged ligands” have broad utility, and also serve as useful starting points for discovery of new enantioselective reactions. There are also several examples of what can be called “privileged catalyst-substrate combinations”, where a catalyst accepts a wide range of structurally diverse but functionally related substrates in highly enantioselective reactions. This lecture will outline my own group's contributions to the discovery and mechanistic elucidation of such privileged systems.