Asymmetric Synthesis of Spiro[Azetidine‐3,3′‐Indoline]‐2,2′‐Diones via Copper(I)‐Catalyzed Kinugasa/C−C Coupling Cascade Reaction
Xianqiang Zhong, Meirong Huang, Huilan Xiong, Yuzhen Liang, Wei Zhou, Qian Cai
Abstract
Spiro[azetidine-indolines] are important scaffolds in diverse bioactive compounds. Current efforts to synthesize spiro[azetidine-indolines] are limited to chiral spiro[azetidine-2,3'-indolines]. Asymmetric synthesis of structurally similar chiral spiro[azetidine-3,3'-indolines] remains unexplored. In this work, the first copper(I)-catalyzed asymmetric Kinugasa/aryl C-C coupling cascade reaction is described. This provides a straightforward access to densely functionalized chiral spiro[azetidine-3,3'-indoline]-2,2'-diones in good yields and with high enantioselectivity.
Topics & Concepts
AzetidineIndolineCascadeCatalysisCopperCascade reactionChemistryCoupling (piping)Coupling reactionCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryMaterials scienceMetallurgyChromatographySynthesis and Catalytic ReactionsSynthesis of β-Lactam CompoundsSynthetic Organic Chemistry Methods