SYNTHESIS OF OPTICALLY-ACTIVE 1,3-DIENES FROM ALKENYLSTANNANES BY A COMBINATION OF ELECTROOXIDATION AND COPPER-MEDIATED HOMOCOUPLING REACTION

Authors
ITOH T EMOTO S KONDO M OHARA H TANAKA H TORII S
Citation
T. Itoh et al., SYNTHESIS OF OPTICALLY-ACTIVE 1,3-DIENES FROM ALKENYLSTANNANES BY A COMBINATION OF ELECTROOXIDATION AND COPPER-MEDIATED HOMOCOUPLING REACTION, Electrochimica acta, 42(13-14), 1997, pp. 2133-2142
Citations number
23
Categorie Soggetti
Electrochemistry
Journal title
Electrochimica acta → ACNP
ISSN journal
00134686
Volume
42
Issue
13-14
Year of publication
1997
Pages
2133 - 2142
Database
ISI
SICI code
0013-4686(1997)42:13-14<2133:SOO1FA>2.0.ZU;2-5
Abstract
A combination of electro-oxidation and copper(II) chloride mediated ho mocoupling of gamma-acyloxyvinylstannanes afforded 1,3-dienes. The ste reoselectivity strongly depended on the solvent system and no isomeriz ation occurred when the reactions were carried out in DMF (0.01 M). Th e facile synthesis of(6R, 11R)-(7E, 9E)-6,11-hexadeca-7,9-dienyl diben zoate was thus accomplished from (R)-(E)-1-tributylstannyl-1-octene-3- ol, which was prepared through the lipase-catalyzed reaction in an opt ically pure form. (C) 1997 Elsevier Science Ltd.