Phosphine-Catalyzed Asymmetric Tandem Isomerization/Annulation of Allyl Amines with Allenoates: Enantioselective Annulation of a Saturated C–N Bond
Leijie Zhou, Xue Zhang, Qijun Wang, Min Liu, Wei Wang, Yongjun Wu, Liezhong Chen, Hongchao Guo
Abstract
Under catalysis by chiral phosphine, an asymmetric isomerization/annulation cascade reaction of allylamines with allenoates was realized. A wide range of γ-substituted allenoates were tolerated to afford chiral pyrroline derivatives in high yields with excellent enantioselectivities. In the reaction, isomerization of readily available N-allylamines to reactive aliphatic imines through a 1,4-proton shift is a key step, which circumvents the isolation of highly unstable alkyl N-sulfonylimines.
Topics & Concepts
AnnulationIsomerizationChemistryPhosphineEnantioselective synthesisCatalysisTandemCascade reactionOrganocatalysisOrganic chemistryCombinatorial chemistryMedicinal chemistryMaterials scienceComposite materialAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry