Abstract
The requirements for a highly selective kinetic resolution with the Sharpless asymmetric dihydroxylation (AD) reaction were investigated with a number of alkene substrates. It was found that with 1-phenyl-4- tert-butylcyclohexene enantioselectivity is very high, yet diastereoselectivity is poor and kinetic resolution is ineffective. With 5-methyl-2-phenylbicyclo[3.2.0]heptan-2-ene both diastereoselectivity and enantioselectivity are high and kinetic resolution is effective. It was discovered that the transition state for the product-determining step in the Sharpless AD reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered.
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