Fluorine-Directed Diastereoselective Iodocyclizations

Authors

  • Matthew Tredwell Dr.,

    1. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865 275 644
    Search for more papers by this author
  • Jennifer A. R. Luft,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA
    Search for more papers by this author
  • Marie Schuler Dr.,

    1. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865 275 644
    Search for more papers by this author
  • Kenny Tenza Dr.,

    1. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865 275 644
    Search for more papers by this author
  • Kendall N. Houk Prof.,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA
    Search for more papers by this author
    • Authors for correspondence: Prof. K. N. Houk for calculations and Dr. V. Gouverneur for synthesis.

  • Véronique Gouverneur Dr.

    1. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865 275 644
    Search for more papers by this author
    • Authors for correspondence: Prof. K. N. Houk for calculations and Dr. V. Gouverneur for synthesis.


  • We are grateful to the EPSRC (M.T.), the National Foundation of South Africa (K.T.), the EU (MEIF CT 2006 03970 (M.S.)), the National Institute of General Medical Sciences, and the National Institutes of Health (GM 36700 to K.N.H.) for financial support. We also thank the NSF-PACI and UCLA-ATS for computing sources.

Abstract

original image

Introvertiertes Fluor: β-Fluorlactone und -tetrahydrofurane werden durch die iodierende Cyclisierung von Allylfluoriden synthetisiert. Der Fluorsubstituent bewirkt als Steuerungsgruppe effizient einen syn-Ringschluss. Experimente und theoretische Studien sprechen dafür, dass die Ausrichtung des Fluoratoms nach innen (siehe Strukturbild) den stereochemischen Verlauf dieser Reaktionen bestimmt.

Ancillary