Enantioselective synthesis of fluorine-containing spiro[indanone-isochromanone] derivatives with contiguous quaternary carbon centers via organocatalytic asymmetric [4 + 2] condensations

Abstract

The stereodivergent synthesis of fluorinated compounds bearing two or more vicinal stereogenic centers constitutes a significant and challenging undertaking. Herein, we report the synthesis of fluorine-containing spiro[indanone-isochromanone] derivatives with contiguous quaternary carbon centers via asymmetric [4 + 2] condensations catalyzed by axially chiral styrene-based organocatalysts. The excellent reactivity and stereocontrol observed in this transformation can be attributed to the unique structural features and catalytic activity of the axially chiral styrene-based organocatalysts.