• The six-membered transistion state is formed by coordination of the Aluminium compound. This cyclic transition state is in the 'chair' conformation. Intramolecularl hydride transfer occurs in this substrate.
  • The reaction is an equilibrium, which can be shifted to the product side by using excess i-PrOH or by removing the acetone byproduct formed in the hydride transfer step.
  • To reverse the equilibrium we can use Al(Oi-Pr)3 and excess acetone. This is known as the Oppenauer oxidation.
  • Aluminium alkoxides are used as they avoid complications from condensation of the aldehyde or ketone enolates.


  • References:
  • Campbell E.J.; Zhou H.; Nguyen S.T.; Organic Letters, 2001, Volume 3, Issue 15, 2391-2393
  • Corma A.; Domine M.E.; Valencia S.; Journal of Catalysis, 2003, Volume 215, Issue 2, 294-304