Subject Sharpless asymmetric hydroxylation

Next, dihydroxylation of homoaUyl alcohol 2.201 was examined for the installation of the stereoselective epoxide (Scheme 2.42). The hydroxyl in 2.201 was protected as the methyl ether 2.202, which was subsequently subjected to Sharpless asymmetric dihydroxylation reaction [149] conditions to afford 2.203, however, no diastereoselectivity was observed and the reaction resulted in the oxidation of the dithiane group under such oxidation reaction conditions. 

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