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Iridium Catalysed Asymmetric Allylic Substitution Reaction of Indolizine Derivatives

Jiamin Lu, Meifang Wang, Ruigang Xu, Haizhou Sun, Xuan Zheng, Guofu Zhong, Xiaofei Zeng

2021Asian Journal of Organic Chemistry19 citationsDOI

Abstract

Abstract A highly efficient direct asymmetric allylic substitution (AAS) reaction of indolizine derivatives with allylic alcohols for accessing enantioenriched indolizine derivatives was realized by combining a chiral iridium complex catalyst with Lewis acid under mild reaction conditions, delivering various chiral allylation products in remarkably high yields and excellent enantioselectivities. This protocol distinguishes itself by availability of the starting materials, mild reaction conditions, broad substrate scope, high yields, excellent selectivity and easy scale‐up in a stereoselective manner, which provides a highly efficient protocol for chiral indolizines.

Topics & Concepts

IndolizineChemistryAllylic rearrangementStereoselectivityIridiumCombinatorial chemistryCatalysisLewis acids and basesSubstitution reactionEnantioselective synthesisSelectivityOrganic chemistrySynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods