Get access

Vinylogous Organocatalytic Triple Cascade Reaction: Forging Six Stereocenters in Complex Spiro-Oxindolic Cyclohexanes

Authors

  • Indranil Chatterjee,

    1. ICIQ – Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34)-977-920-823; phone: (+34)-977-920-207
    Search for more papers by this author
  • David Bastida,

    1. ICIQ – Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34)-977-920-823; phone: (+34)-977-920-207
    Search for more papers by this author
  • Paolo Melchiorre

    Corresponding author
    1. ICIQ – Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34)-977-920-823; phone: (+34)-977-920-207
    2. ICREA – Institució Catalana de Recerca i Estudis Avançats, Pg. Lluís Companys 23, 08010 Barcelona, Spain
    • ICIQ – Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain, Fax: (+34)-977-920-823; phone: (+34)-977-920-207

    Search for more papers by this author

Abstract

We report a triple vinylogous cascade reaction, yielding valuable spiro-oxindolic cyclohexane derivatives. The three-component domino process proceeds by way of a catalyzed Michael/1,6-addition/vinylogous aldol sequence affording the products with six stereogenic centers and very high control over the stereochemistry. The chemistry is based on a rare example of asymmetric 1,6-addition to linear 2,4-dienals proceeding with complete δ-site selectivity. Key to the reaction development was a directing group positioned at the β-dienal position, which was essential for achieving highly predictable reaction outcomes.

original image
Get access to the full text of this article

Ancillary