Advertisement

Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene

Authors

  • Mohamed F. El-Mansy,

    1. Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881 (USA), Fax: (+1) 414-288-7066
    Search for more papers by this author
  • Dr. Anobick Sar,

    1. Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881 (USA), Fax: (+1) 414-288-7066
    Search for more papers by this author
  • Dr. Sergey Lindeman,

    1. Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881 (USA), Fax: (+1) 414-288-7066
    Search for more papers by this author
  • Dr. William A. Donaldson

    Corresponding author
    1. Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881 (USA), Fax: (+1) 414-288-7066
    • Department of Chemistry, Marquette University, P.O. Box 1881, Milwaukee, Wisconsin 53201-1881 (USA), Fax: (+1) 414-288-7066
    Search for more papers by this author

Abstract

The racemic (6-cyclo-heptadienyl)Fe(CO)3+ cation ((±)-7), prepared from cyclooctatetraene, was treated with a variety of carbon and heteroatom nucleophiles. Attack took place at the less hindered C1 dienyl carbon and decomplexation of the (cycloheptadiene)Fe(CO)3 complexes gave products rich in functionality for further synthetic manipulation. In particular, a seven-step route was developed from racemic (6-styryl-2,4-cycloheptadien-1-yl)phthalimide ((±)-9 d) to afford the optically active aminocycloheptitols (−)-20 and (+)-20.

Ancillary