Highly enantioselective synthesis of 1,3-mercapto alcohols from α,β-unsaturated ketones: asymmetric bifunctional group exchange reaction

Optically active 1,3-mercapto alcohols were synthesized from α,β-unsaturated ketones using a chiral reagent B and dimethylaluminum chloride in two steps. The transformation involved a tandem Michael addition–MPV reduction and a base-catalyzed elimination. The two newly created chiral carbons in trans-chalcone derivatives were enantioselectively controlled to a high degree. Using the above transformation, an asymmetric bifunctional group exchange reaction between the substrate and chiral reagent was developed.