Three-Pot Synthesis of Chiral Anti-1,3-diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Epoxidation and Reductive Opening of the Epoxide.

Abstract

A three-pot asymmetric synthesis of the anti-1,3-diol unit was developed. In the first pot, enantioselective aldol reaction of aldehydes proceeds, catalyzed by organocatalyst, followed by either Wittig or Horner-Wadsworth-Emmons reactions to afford δ-hydroxy α,β-unsaturated carbonyls with excellent enantioselectivity. Diastereoselective hydroxy-directed anti-epoxidation proceeds in the next pot by the use of tert-BuOOH and LiHMDS. Reductive opening of the epoxide proceeds in a third pot to afford anti-β,δ-hydroxy carbonyl compounds with excellent diastereo- and enantioselectivity.