Hamon, David P. G.Tuck, Kellie LouiseChristie, Hamish Saul2007-02-252007-02-252001Tetrahedron, 2001; 57(46):9499-95080040-4020http://hdl.handle.net/2440/4871Available online 5 November 2001.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. It was discovered that the transition state for the product-determining step in the Sharpless asymmetric dihydroxylation reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered.enCopyright © 2001 Elsevier Science Ltd. All rights reserved.sharpless asymmetric dihydroxylation ; kinetic resolutions ; transition stateJournal article002001036510.1016/S0040-4020(01)00948-6