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Synthesis of Optically Active 1,3-Dienes from Alkenylstannanes by a Combination of Electro-Oxidation and Copper-Mediated Homocoupling Reaction

  • Toshiyuki Itoh
  • Sachie Emoto
  • Hideo Tanaka
  • Shigeru Torii
Conference paper

Abstract

The copper(II) salt mediated reaction of alkenylstannanes was reported to provide high stereospecificity for the homocoupling reaction to symmetrical dienes, though it required at least a stoichiometric amount of copper salt.1 Because of its highly stereoselective nature, we refined the copper-mediated coupling reaction of alkenylstannanes using electro-oxidation; the stereocontrolled synthesis of optically active diene 2 from alkenylstannane 1 was accomplished using catalytic amounts of Cu(II)C12 in combination with electro-oxidation (Eq. 1).2

Keywords

Copper Catalyst Benzyl Ether Tetrabutylammonium Perchlorate Electroorganic Synthesis High Stereospecificity 
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Copyright information

© Springer Japan 1998

Authors and Affiliations

  • Toshiyuki Itoh
    • 1
  • Sachie Emoto
    • 1
  • Hideo Tanaka
    • 2
  • Shigeru Torii
    • 2
  1. 1.Department of Chemistry, Faculty of EducationOkayama UniversityOkayama 700Japan
  2. 2.Department of Applied Chemistry, Faculty of EngineeringOkayama UniversityOkayama 700Japan

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