Acetone → HCID 820605, compound

Participants

Reaction Steps

Alternatively, 1,2-dihydronaphthalene (V) is treated with OsO4 and NMMO in a suitable solvent, such as a mixture of acetone and water, at -60° to +20° C., preferably at about 0° C., for 10 to 48 hours, preferably about 26 hours, to give cis-1,2,3,4-tetrahydro-1,2-napthalenediol. The treatment with OsO4 and NMMO can optionally be carried out in the presence of hydroquinine 4-chlorobenzoate, as described in Sharpless, et al, J. Org. Chem., 57, 2768-2771 (1992), in which case predominantly one enantiomer of the cis-diol is produced. The diol is treated with (C6H5)3PBr2 in the presence of a tertiary amine base, preferably triethylamine, in a suitable solvent, such as CH3CN, at 0° to 50° C., preferably at about 25° C., for 10 to 30 hours, preferably about 20 hours, to form predominantly one enantiomer of the epoxide VI, having the absolute stereochemistry indicated in Reaction Scheme C.

Provenance & Evidence