Asymmetric Addition Reactions with Optimized Selenium Electrophiles

Authors

  • Dr. Thomas Wirth,

    Corresponding author
    1. Institut für Organische Chemie, Universität Basel St. Johanns-Ring 19, CH-4056 Basel (Switzerland) Fax: Int. code +(61)267-1105
    • Institut für Organische Chemie, Universität Basel St. Johanns-Ring 19, CH-4056 Basel (Switzerland) Fax: Int. code +(61)267-1105
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  • Dipl.-Chem. Gianfranco Fragale

    1. Institut für Organische Chemie, Universität Basel St. Johanns-Ring 19, CH-4056 Basel (Switzerland) Fax: Int. code +(61)267-1105
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Abstract

The synthesis of various nonracemic diselenides by different methods is described. These diselenides are precursors for optically active selenium electrophiles. Their facial selectivity upon addition to styrene was investigated with respect to the chiral moiety neighboring the selenium. Diselenides 1 i, 1 n, and 1 v yielded addition products 7 with diastereomeric excesses up to 95%. Some diselenides, intermediates, and products of the addition reaction were investigated by 77Se NMR spectroscopy.

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