Asymmetric Synthesis of α-Spiro-γ-lactones and α-Substituted γ-Lactones via Chiral Bifunctional Sulfide-Catalyzed Bromolactonizations.

ABSTRACT

An efficient enantioselective synthesis of γ-chiral α-spiro-γ-lactones, which are important building blocks for pharmaceuticals, was achieved via BINOL-derived chiral bifunctional sulfide-catalyzed bromolactonizations of α-allyl carboxylic acids containing either hetero- or carbocyclic structures. Transformations of the resultant α-spiro-type bromolactonization product were examined to obtain optically active γ-functionalized α-spiro-γ-lactones. The utility of this catalytic system was also demonstrated in the asymmetric synthesis of α,α-diaryl- and dialkyl-substituted γ-lactones.