Synthesis of optically active 1,3-dienes from alkenylstannanes by a combination of electro-oxidation and copper-mediated homocoupling reaction

Toshiyuki Itoh, Sachie Emoto, Michiyo Kondo, Hiroyuki Ohara, Hideo Tanaka, Shigeru Torii

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12 Citations (Scopus)

Abstract

A combination of electro-oxidation and copper(II) chloride mediated homocoupling of γ-acyloxyvinylstannanes afforded 1,3-dienes. The stereoselectivity strongly depended on the solvent system and no isomerization occurred when the reactions were carried out in DMF (0.01 M). The facile synthesis of (6R, 11R)-(7E, 9E)-6,11-hexadeca-7,9-dienyl dibenzoate was thus accomplished from (R)-(E)-1-tributylstannyl-1-octene-3-ol, which was prepared through the lipase-catalyzed reaction in an optically pure form.

Original languageEnglish
Pages (from-to)2133-2142
Number of pages10
JournalElectrochimica Acta
Volume42
Issue number13-14
Publication statusPublished - 1997

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Keywords

  • Cu-mediated reaction
  • Electro-oxidation
  • Optically active 1,3-diene
  • Vinylstannanes

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Analytical Chemistry
  • Electrochemistry

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