Concerning kinetic resolution by the Sharpless asymmetric dihydroxylation reaction

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Hamish S. Christie, David P. G. Hamon and Kellie L. Tuck


Abstract

The transition state for the product-determining step in the Sharpless asymmetric dihydroxlation reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered.


References

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  15. The radical inhibitor, 2,6-di-tert-butyl-p-cresol, was added during the work-up procedure, otherwise much lower yields of this alkene were obtained.
  16. In the 1H NMR spectrum, methoxy resonances at δ 3.37 and 3.53 for the diastereomers produced from the racemic diol showed separation at the base-line.
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