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

Research output: Contribution to journalArticle

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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Stereoselectivity
Electrooxidation
Lipases
Isomerization
Lipase
Copper
cupric chloride
1-octene

Keywords

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

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Analytical Chemistry
  • Electrochemistry

Cite this

Synthesis of optically active 1,3-dienes from alkenylstannanes by a combination of electro-oxidation and copper-mediated homocoupling reaction. / Itoh, Toshiyuki; Emoto, Sachie; Kondo, Michiyo; Ohara, Hiroyuki; Tanaka, Hideo; Torii, Shigeru.

In: Electrochimica Acta, Vol. 42, No. 13-14, 1997, p. 2133-2142.

Research output: Contribution to journalArticle

Itoh, Toshiyuki ; Emoto, Sachie ; Kondo, Michiyo ; Ohara, Hiroyuki ; Tanaka, Hideo ; Torii, Shigeru. / Synthesis of optically active 1,3-dienes from alkenylstannanes by a combination of electro-oxidation and copper-mediated homocoupling reaction. In: Electrochimica Acta. 1997 ; Vol. 42, No. 13-14. pp. 2133-2142.
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AU - Ohara, Hiroyuki

AU - Tanaka, Hideo

AU - Torii, Shigeru

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