93156-53-7Relevant academic research and scientific papers
An investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reaction
Hamon, David P.G,Tuck, Kellie L,Christie, Hamish S
, p. 9499 - 9508 (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.
