Posts Tagged ‘asymmetric epoxidation’

Why is the Sharpless epoxidation enantioselective? Part 1: a simple model.

Sunday, December 9th, 2012

Sharpless epoxidation converts a prochiral allylic alcohol into the corresponding chiral epoxide with > 90% enantiomeric excess[1],[2]. Here is the first step in trying to explain how this magic is achieved.



  1. J.M. Klunder, S.Y. Ko, and K.B. Sharpless, "Asymmetric epoxidation of allyl alcohol: efficient routes to homochiral .beta.-adrenergic blocking agents", J. Org. Chem., vol. 51, pp. 3710-3712, 1986.
  2. R.M. Hanson, and K.B. Sharpless, "Procedure for the catalytic asymmetric epoxidation of allylic alcohols in the presence of molecular sieves", J. Org. Chem., vol. 51, pp. 1922-1925, 1986.