Regio- and Stereoselective Electrophilic C-Substitution of 2-(N,N-Dibenzylamino)-1,ω-alkanediols by Lithiation of Their Carbamates

Authors

  • Walter Guarnieri,

    1. Organisch-chemisches Institut der Universität, Corrensstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-9772
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  • Dr. Matthias Grehl,

    1. Organisch-chemisches Institut der Universität, Corrensstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-9772
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    • X-ray structure analysis

  • Prof. Dr. Dieter Hoppe

    Corresponding author
    1. Organisch-chemisches Institut der Universität, Corrensstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-9772
    • Organisch-chemisches Institut der Universität, Corrensstrasse 40, D-48149 Münster (FRG), Telefax: Int. code + (251)83-9772
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  • This research was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the Pharma Research Center of Bayer AG, Wuppertal.

  • Dedicated to Professor Werner Tochtermann on the occasion of his 60th birthday

Abstract

original image

A flexible system of building blocks can be used for the synthesis of the potential enzyme inhibitors 1 and 2 (n = 1, 2) in high enantiomeric purity. The regiochemistry of the deprotonation is determined by the reaction conditions. 1, ω-Alkanediols 1 and 2 are available from (S)-aspartic and (S)-glutamic acid, respectively; a variety of electrophiles El can be added at C-1 or C-ω.

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