The first example of enantioselective protonation of prochiral enolates with chiral γ-hydroxyselenoxides

Article abstract of DOI:10.1246/cl.1996.207

Enantioselective protonation of a simple enolate has been developed using an optically pure γ-hydroxyselenoxide 1 as a chiral proton source. Reaction of zinc bromide enolate 7b with (S_se)-selenoxide (S_se)-1c gave (S)-2-benzylcyclohexanone (S)-8 with high enantioselectivity. Intramolecular hydrogen bonding between hydroxy group and seleninyl-oxygen of 1 would contribute to this asymmetric induction.