Highly Stereo- and Regio-Selective Intramolecular Cyclization with Diastereoselective Asymmetric Induction by Electroreduction of Optically Active <i>N</i>-Alkenyl-2-Acylpyrrolidines

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Abstract

Electroreduction of optically active (<i>S</i>)- and (<i>R</i>)-<i>N</i>-(3-butenyl)(or (<i>R</i>)-<i>N</i>-benzyl)-2-acetylpyrrolidines (<b>1a</b>) and (<b>1b</b>) (or (<b>2b</b>)) were carried out in <i>N</i>,<i>N</i>-dimethylformamide containing Et<sub>4</sub>NOTs as a supporting electrolyte, which brought about highly stereo- and regioselective intramolecular cyclization with diastereoselective asymmetric induction to give the corresponding (4<i>S</i>,5<i>R</i>,6<i>S</i>)- and (4<i>R</i>,5<i>S</i>,6<i>R</i>)-<i>cis</i>-4,5-dimethyl-1-azabicyclo[4.3.0]nonan-5-ols (<b>3a</b>) and (<b>3b</b>) (or (8<i>R</i>,9<i>S</i>,10<i>R</i>)-9-methyl-1-azatricycro[8.3.0<sup>1,10</sup>.0<sup>3,8</sup>]tridecane-9-ol-3,6-diene (<b>4b</b>)) in 66% and 49% (or 31%) yields, respectively.

Journal

  • Electrochemistry

    Electrochemistry 79(6), 447-449, 2011

    The Electrochemical Society of Japan

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