Sharpless Asymmetric Dihydroxylation on an Industrial Scale

It is shown in this study that the inexpensive N-methylmorpholine N-oxide can be successfully employed as a reoxidant in the Sharpless asymmetric dihydroxylation reaction on a large scale. The reaction of o-isopropoxy-m-methoxystyrene on a 2 kg scale gave the corresponding diol in high yield and high enantiomeric excess. The extension of this synthetic method to other olefins is also presented.