Enantioselective γ-Addition-Driven Cascade of β,γ-Unsaturated Ketones by Ion-Pair Catalysis: Access to Chiral 1,3-Dioxolochroman Scaffolds

A highly enantioselective.-addition-driven cascade of beta,gamma-unsaturated carbonyl compounds by bifunctional ion-pair catalysis has been developed. With this protocol, a range of functionalized chiral 1,3-dioxolochroman derivatives were prepared in high yields with superior stereoselectivities (>99% ee and >20:1 dr). The utility of this method was demonstrated by one-pot synthesis, scaled-up preparation, and facile transformation. Moreover, mechanistic investigations provided insights into the reaction pathway and the origin of chiral induction.

Automated summary

A highly enantioselective cascade reaction of beta,gamma-unsaturated carbonyl compounds using bifunctional ion-pair catalysis has been developed, resulting in functionalized chiral 1,3-dioxolochroman derivatives with high yields and excellent stereoselectivities. The utility of this method was demonstrated through one-pot synthesis, scaled-up preparation, and facile transformation. Mechanistic investigations provided insights into the reaction pathway and chiral induction.