Ln(III)/Chiral Brønsted Acid Catalyzed Asymmetric Cascade Ring Opening/Aza-Piancatelli Rearrangement of D–A Cyclopropanes
Lei Xu, Qian Yang, Sishi Zhong, Hongxiang Li, Yurong Tang, Yunfei Cai
Abstract
The first Lewis acid and chiral Brønsted acid cooperatively catalyzed asymmetric cascade ring opening/aza-Piancatelli rearrangement reaction of furyl-substituted donor-acceptor cyclopropanes is achieved, enabling the construction of functionalized aminocyclopentenones bearing α-quaternary carbon stereocenters in high yields with excellent enantio- and diastereoselectivities under remarkably low catalyst loading of 0.2-1.2 mol %.
Topics & Concepts
ChemistryCascadeRing (chemistry)Brønsted–Lowry acid–base theoryCatalysisStereochemistryMedicinal chemistryOrganic chemistryChromatographyCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods