Diastereoselective Synthesis of Protected Syn 1,3-Diols by Base-Catalyzed Intramolecular Conjugate Addition of Hemiacetal-Derived Alkoxide Nucleophiles

Article abstract of DOI:10.1021/jo00061a018

Reaction of the illustrated unsaturated hydroxy esters (X = OMe, R₂ = H, Me) and amides (X = N(Me)OMe, R₂ = H, Me) with benzaldehyde and potassium alkoxide or amide bases is reported.The resulting benzylidene acetals are obtained in