Substrate‐Controlled Regioselectivity Switch in a Three‐Component 1,3‐Dipolar Cycloaddition Reaction to Access 3,3′‐Pyrrolidinyl‐Spirooxindoles Derivatives
Kai‐Kai Wang, Yan‐Li Li, Rongxiang Chen, Ai‐Li Sun, Zhan‐Yong Wang, Ying‐Chao Zhao, Mingyue Wang, Shi Sheng
Abstract
Abstract The additive‐free 1,3‐dipolar cycloaddition reaction of isatin‐derived azomethine ylides with α‐cyano‐α,β‐unsaturated compounds was developed, which enabled diversity‐oriented synthesis of a series of novel and structurally complex 3,3′‐pyrrolidinyl‐spirooxindoles derivatives containing four contiguous and two quaternary stereogenic centers in high yields (up to 92%) and excellent diastereoselectivities (up to >25:1 dr). The reaction displays switchable regioselectivity depending on the steric effect of the substrates. magnified image
Topics & Concepts
RegioselectivityChemistryStereocenterIsatinCycloadditionSteric effects1,3-Dipolar cycloadditionSubstrate (aquarium)Combinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisCatalysisOceanographyGeologyCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods