Get access
Advertisement

A Priori Theoretical Prediction of Selectivity in Asymmetric Catalysis: Design of Chiral Catalysts by Using Quantum Molecular Interaction Fields

Authors

  • James C. Ianni Dr.,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA, Fax: (+1) 215-573-7165
    Search for more papers by this author
  • Venkatachalam Annamalai,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA, Fax: (+1) 215-573-7165
    Search for more papers by this author
  • Puay-Wah Phuan Dr.,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA, Fax: (+1) 215-573-7165
    Search for more papers by this author
  • Manoranjan Panda Dr.,

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA, Fax: (+1) 215-573-7165
    Search for more papers by this author
  • Marisa C. Kozlowski Prof.

    1. Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA, Fax: (+1) 215-573-7165
    Search for more papers by this author

  • Financial support of this research was provided by the NIH (GM59945). Computing resources from the NCSA (CHE020059) and the NSF CRIF program (CHE0131132) are acknowledged. We thank Steve Dixon, Giorgio Lauri, and Prof. Kenneth Merz for assistance with the QM-QSAR program. We are grateful to Bill Nugent for supplying the unpublished data for P3.

Abstract

original image

Excellent forecast: The selectivities for a set of chiral catalysts were predicted by methods derived from quantum mechanical molecular interaction fields that were applied to ground-state structures rather than transition-state structures. The predictions for the asymmetric addition of Et2Zn to PhCHO are in remarkable agreement with the experimental results (equation image=0.87).

Get access to the full text of this article

Ancillary