The product stereochemistry can be predicted using the model shown in Scheme 5.

Scheme 5

Application

The reaction has been applied for the synthesis of a number of natural products, antibiotics and pharmaceuticals. For examples, the synthesis of the sex pheromone of gypsy moth (Lymantria dispar) (+)-disparlure 12 has been accomplished (Scheme 6). The epoxidation of allyl alcohol 7 by Sharpless procedure affords optically active epoxy alchohol 8 with 95% ee that in presence of pyridinium dichlorochromate (PDC) gives chiral aldehyde 9 . The latter with Wittig salt 10 affords trans -alkene 11 that could be reduced using Pd/C to give the target (+)-disparlure 12 .

Scheme 6

The Scheme 7 shows the use of the Sharpless asymmetric epoxidation for the synthesis of gastric inhibitor (S) -propanolol. The epoxidation of 3-(trimethylsilyl) prop-2-en-1-ol 13 affords epoxy alcohol 14 with 90% ee that could be converted into 16 by mesylation 15 followed by coupling with 1-naphthol. Opening of the epoxide 16 with isopropylamine leads to the formation of the target (S) -propanolol 17 .

Scheme 7