Enantioselective Alkynylation of 2‐Aryl‐3<i>H</i>‐indol‐3‐ones via Cooperative Catalysis of Copper/Chiral Phosphoric Acid
Xixi Wu, Tao Ma, Xiu‐Xiu Qiao, Changpeng Zou, Ganpeng Li, Yonghui He, Xiaojing Zhao
Abstract
A facile enantioselective alkynylation of cyclic ketimines attached to a neutral functional group utilizing the dual Cu(I)-CPA catalysis is described. The strategy of the alkynylation of 2-aryl-3H-indol-3-one directly to chiral propargylic amines containing indolin-3-one moiety in good yields and enantioselectivities. Moreover, gram-scale synthesis of chiral propargylamines based C2-quaternary indolin-3-ones was performed. The synthetic applications were confirmed by transformations of the products with no decrease in the yield and enantioselectivity.
Topics & Concepts
Enantioselective synthesisAlkynylationMoietyArylPhosphoric acidChemistryCatalysisYield (engineering)Combinatorial chemistryOrganic chemistryMaterials scienceAlkylMetallurgyAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions