Patent ID: 6852874

Claim:
A process for catalyzing a second-cycle asymmetric dihydroxylation reaction for converting an olefin substrate to a chiral vicinal diol product, said process comprising the following steps: Step A: mixing the olefin substrate with a catalytic amount of a chiral bidentate ligand in an aqueous solvent, the aqueous solvent optionally being an alcohol/water solvent mixture, the chiral bidentate ligand being represented by the following structure: wherein: R is a radical selected from the group consisting of hydrogen, carboxylic acid, phenyl, 1-naphthyl, 2-naphthyl, alkyl(C 1 -C 12 ), cyclo-alkyl(C 3 -C 12 ), carbamoyl, N-alkyl(C 1 -C 12 ) carbamoyl, and N,N-alkyl(C 1 -C 12 ) carbamoyl, wherein the phenyl, 1-naphthyl, and 2-naphthyl radicals ay optionally have substituents in any available position; R 1 is a radical selected from the group consisting of carboxylic acid, carbamoyl, N-alkyl(C 1 -C 12 ) carbamoyl, and N,N-dialkyl(C 1 -C 12 ) carbamoyl; R 2 is a radical selected from the group consisting of hydrogen , alkyl(C 1 -C 12 ), aryl, and heteroaryl; and X and Y are radicals independently selected from the group consisting of hydroxyl, amino, N-alkyl(C 1 -C 12 )sulfonylamino, N-arylsulfonylamino, and N-heteroarylsulfonylamino; with the following provisos: if X is not a hydroxyl group, then Y must be a hydroxy group; if Y is not a hydroxyl group then X must be a hydroxyl group; and at least one of the following must be a carboxylic acid group: R, R 1 or R 2 ; and then Step B: adding to the mixture of said Step A a stoichiometric amount or a stoichimetric excess of N-methyl morpholine N-oxide with respect to the olefin substrate and a catalytic amount of osmium tetraoxide under reaction conditions for catalyzing the second-cycle asymmetric dihydroxylation reaction for converting the olefin substrate to the chiral vicinal diol product.