Base-Promoted Formal (3 + 2) Cycloaddition of α-Halohydroxamates with Electron-Deficient Alkenyl-iminoindolines To Synthesize Spiro-indolinepyrrolidinones
Xiang Zhang, Hai-Yu Dai, Wan-Cong Liu, Rong Zeng, Zhen Dai, Yapeng Wang, Jun‐Long Li, Qing‐Zhu Li, Bo Han
Abstract
Construction of pyrrolidinyl-spiroindoles with easily available starting materials has attracted considerable attention from the synthesis community and is in great demand. Here, we describe a base-promoted formal (3 + 2) cycloaddition of α-halohydroxamates with alkenyl-iminoindolines. The present methodology features mild reaction conditions and a broad substrate scope with up to 99% yield and excellent diastereoselectivity. The versatility of this approach is demonstrated through valuable synthetic transformations. Preliminary mechanistic studies shed light on the mechanism of this cycloaddition process.
Topics & Concepts
CycloadditionChemistryScope (computer science)Formal synthesisYield (engineering)Combinatorial chemistrySubstrate (aquarium)Organic chemistryCatalysisComputer scienceProgramming languageOceanographyGeologyMetallurgyMaterials scienceSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Synthesis and Catalysis