New ligands for asymmetric dihydroxylation: multiple...

C - Chemistry – Metallurgy – 07 – D

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C07D 453/04 (2006.01) C07C 29/48 (2006.01) C07C 31/20 (2006.01) C07C 33/26 (2006.01) C07C 67/31 (2006.01) C07C 69/675 (2006.01) C07D 317/10 (2006.01)

Patent

CA 2120919

Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt, and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.

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