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

doi:10.1016/S0013-4686(97)85490-4

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

Faculty of Engineering

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	2133-2142
Number of pages	10
Journal	Electrochimica Acta
Volume	42
Issue number	13-14
DOIs	https://doi.org/10.1016/S0013-4686(97)85490-4
Publication status	Published - 1997

Keywords

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

ASJC Scopus subject areas

Chemical Engineering(all)
Electrochemistry

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10.1016/S0013-4686(97)85490-4

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

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.",

keywords = "Cu-mediated reaction, Electro-oxidation, Optically active 1,3-diene, Vinylstannanes",

author = "Toshiyuki Itoh and Sachie Emoto and Michiyo Kondo and Hiroyuki Ohara and Hideo Tanaka and Shigeru Torii",

note = "Funding Information: This work was supportedb y a Grant-in-Aid for ScientificR esearcho n Priority Areas,“ New Development of Organic Electrochemistry”N o. 06226252, from the Ministry of Education,S ciencea nd Culture of Japan. The authorsa reg ratefult o ProfessorsK enji Uneyama, Yasuo Nakao and Takashi Sakai of Okayama University for their valuable discussions throughoutt his work. They are also gratefult o the SC-NMR Laboratory of Okayama University for the NMR measurements.",

year = "1997",

doi = "10.1016/S0013-4686(97)85490-4",

language = "English",

volume = "42",

pages = "2133--2142",

journal = "Electrochimica Acta",

issn = "0013-4686",

publisher = "Elsevier Limited",

number = "13-14",

}

TY - JOUR

T1 - Synthesis of optically active 1,3-dienes from alkenylstannanes by a combination of electro-oxidation and copper-mediated homocoupling reaction

AU - Itoh, Toshiyuki

AU - Emoto, Sachie

AU - Kondo, Michiyo

AU - Ohara, Hiroyuki

AU - Tanaka, Hideo

AU - Torii, Shigeru

N1 - Funding Information: This work was supportedb y a Grant-in-Aid for ScientificR esearcho n Priority Areas,“ New Development of Organic Electrochemistry”N o. 06226252, from the Ministry of Education,S ciencea nd Culture of Japan. The authorsa reg ratefult o ProfessorsK enji Uneyama, Yasuo Nakao and Takashi Sakai of Okayama University for their valuable discussions throughoutt his work. They are also gratefult o the SC-NMR Laboratory of Okayama University for the NMR measurements.

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

KW - Cu-mediated reaction

KW - Electro-oxidation

KW - Optically active 1,3-diene

KW - Vinylstannanes

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U2 - 10.1016/S0013-4686(97)85490-4

DO - 10.1016/S0013-4686(97)85490-4

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AN - SCOPUS:0030674246

SN - 0013-4686

VL - 42

SP - 2133

EP - 2142

JO - Electrochimica Acta

JF - Electrochimica Acta

IS - 13-14

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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