Regio- and Stereoselective Synthesis of Dispiro-bisoxindoles via [3+2] Annulation Involving Nitroisatylidene as a Vinylogous Michael Donor
Chenikkayala Siva Sankara, Irishi N. N. Namboothiri
Abstract
A cascade [3+2] annulation, involving a γ-selective vinylogous Michael addition of nitroalkylideneoxindoles to various electron deficient alkenes followed by an intramolecular Michael addition, provides access to dispiro-bis-oxindoles and spiro-oxindoles. Up to four contiguous chiral centers, including two quaternary spirocenters, are generated in this high-yield regio- and diastereoselective transformation that also provides a convenient entry into conformationally constrained γ-amino acid derivatives.
Topics & Concepts
AnnulationChemistryMichael reactionIntramolecular forceStereoselectivityStereochemistryYield (engineering)CascadeOrganic chemistryCatalysisChromatographyMaterials scienceMetallurgyAsymmetric Synthesis and CatalysisSynthesis and Catalytic ReactionsSynthetic Organic Chemistry Methods