Enantioselective Organocatalytic Three-Component Vinylogous Michael/Aldol Tandem Reaction among 3-Alkylidene oxindoles, Methyleneindolinones, and Aldehydes
Jing-Xiang Xu, Yi-Syun Jiang, Chih‐Hao Chen, Nadaraj Sathishkumar, Kai‐Ti Chu, Ming‐Hsi Chiang, Hsin‐Tsung Chen, Jeng‐Liang Han
Abstract
We reported a one-pot enantioselective three-component vinylogous Michael/aldol tandem reaction of prochiral 3-alkylidene oxindoles with methyleneindolinones and aldehydes using bifunctional organocatalysts. A variety of enantioenriched 3,3-disubstituted oxindoles 3 and spirolactones 4 were generated in moderate yields (up to 78%) with high stereoselectivities (up to >20:1 dr, >99% ee). Intriguingly, we observed that the aldol reaction with paraformaldehyde generates 3,3-disubstituted oxindoles 3 bearing a hydroxymethyl group, while the reaction with aliphatic aldehydes generates spirolactones 4.
Topics & Concepts
Aldol reactionChemistryEnantioselective synthesisBifunctionalTandemHydroxymethylCascade reactionOrganic chemistryMichael reactionOrganocatalysisAldehydeCatalysisStereochemistryComposite materialMaterials scienceAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions