Zuschrift

Fluorine-Directed Diastereoselective Iodocyclizations†

  1. Matthew Tredwell Dr.1,
  2. Jennifer A. R. Luft2,
  3. Marie Schuler Dr.1,
  4. Kenny Tenza Dr.1,
  5. Kendall N. Houk Prof.2,‡,
  6. Véronique Gouverneur Dr.1,‡

Article first published online: 16 NOV 2007

DOI: 10.1002/ange.200703465

Issue

Angewandte Chemie

Angewandte Chemie

Volume 120, Issue 2, pages 363–366, December 28, 2007

Additional Information

How to Cite

Tredwell, M., Luft, Jennifer A. R., Schuler, M., Tenza, K., Houk, Kendall N. and Gouverneur, V. (2008), Fluorine-Directed Diastereoselective Iodocyclizations. Angew. Chem., 120: 363–366. doi: 10.1002/ange.200703465

Author Information

  1. 1

    Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK, Fax: (+44) 1865 275 644

  2. 2

    Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA

  1. ‡

    Authors for correspondence: Prof. K. N. Houk for calculations and Dr. V. Gouverneur for synthesis.

  1. †

    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.

  2. ‡

    Authors for correspondence: Prof. K. N. Houk for calculations and Dr. V. Gouverneur for synthesis.

Publication History

  1. Issue published online: 19 DEC 2007
  2. Article first published online: 16 NOV 2007
  3. Manuscript Received: 31 JUL 2007

Funded by

  • EPSRC
  • National Foundation of South Africa
  • EU. Grant Number: MEIF CT 2006 03970
  • National Institute of General Medical Sciences
  • National Institutes of Health. Grant Number: GM 36700
  • NSF-PACI
  • UCLA-ATS

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Keywords:

  • Dichtefunktionalrechnungen;
  • Fluor;
  • Lactone;
  • Stereoelektronische Effekte;
  • Tetrahydrofurane
Thumbnail image of graphical abstract

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.

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