Get access
Advertisement

Organocatalytic Conjugate Addition of Malonates to α,β-Unsaturated Aldehydes: Asymmetric Formal Synthesis of (−)-Paroxetine, Chiral Lactams, and Lactones

Authors

  • Sven Brandau Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
    Search for more papers by this author
  • Aitor Landa Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
    Search for more papers by this author
  • Johan Franzén Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
    Search for more papers by this author
  • Mauro Marigo Dr.,

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
    Search for more papers by this author
  • Karl Anker Jørgensen Prof. Dr.

    1. The Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C, Denmark, Fax: (+45) 8919-6199
    Search for more papers by this author

  • This work was made possible by a grant from The Danish National Research Foundation. A.L. thanks Eusko Jaurlaritza/Gobierno Vasco for financial support (postdoctoral fellowship). J.F. thanks The Wenner–Gren Foundation for a grant. Thanks are expressed to Dr. Jacob Overgaard from the Department of Chemistry, Aarhus University for performing the X-ray crystal structure analysis.

Abstract

original image

In addition: The scope of the title reaction is demonstrated by the synthesis of chiral lactones and lactams. The latter class of compounds is very important for the preparation of the pharmaceutical compounds such as (−)-paroxetine and (+)-femoxetine.

Get access to the full text of this article

Ancillary