Asymmetric Sequential Vinylogous Mannich/Annulation/Acylation Process of 2‐Ethylidene 1,3‐Indandiones and Isatin <i>N</i>‐Boc Ketimines: Access to Chiral Spiro‐Oxindole Piperidine Derivatives
I‐Ting Chen, Ren‐You Guan, Jeng‐Liang Han
Abstract
Abstract A catalytic asymmetric vinylogous Mannich/annulation/acylation reaction of 2‐ethylidene 1,3‐indandiones with isatin N ‐Boc ketimines has been developed, which furnished a series of chiral spiro‐oxindole piperidine derivatives with polyaromatic scaffolds in 30–67% yield and 93–98% ee . The DFT computational calculation is used to probe and explain the origin of the enantioselectivity and observed formation of O ‐acetylated products. magnified image
Topics & Concepts
ChemistryAnnulationIsatinPiperidineAcylationOxindoleMannich reactionYield (engineering)CatalysisOrganic chemistryMedicinal chemistryStereochemistryMetallurgyMaterials scienceAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods