Enantioselective γ-Addition-Driven Cascade of β,γ-Unsaturated Ketones by Ion-Pair Catalysis: Access to Chiral 1,3-Dioxolochroman Scaffolds
Xuemei Wang, Liang Zhou, Hongkui Zhang, Xiaoyu Ren, Guowei Gao, Tianli Wang
Abstract
A highly enantioselective γ-addition-driven cascade of β,γ-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.
Topics & Concepts
Enantioselective synthesisChemistryBifunctionalCascadeCatalysisCombinatorial chemistryAsymmetric inductionOrganic chemistryChromatographySynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis