Preparation of Selanyl-Substituted Conjugated Enynes by Copper-Catalysed Coupling Reaction of ( E )-γ-Selanyl Vinylzirconocene with Acetylenic Bromide †
Free accessResearch articleFirst published online September, 2003
Preparation of Selanyl-Substituted Conjugated Enynes by Copper-Catalysed Coupling Reaction of ( E )-γ-Selanyl Vinylzirconocene with Acetylenic Bromide †
A stereoselective synthesis of conjugated enynes containing allyl selenide unit is reported. Selanyl-substituted conjugated enynes were obtained by the coupling reaction of (E)-γ-selanyl vinylzirconocene with acetylenic bromide in the presence of CuCl.
PirguliyevN.Sh., BrelV. K., SefirovN. S., and StangP. J., Tetrahedron, 1999, 55, 12377.
2.
MaY., and HuangX., Synth. Commun., 1997, 27, 3441 and references cited therein.
3.
(a) NussbaunerP., LeitnerL., MrazK., and StutzA., J. Med. Chem., 1995, 38, 1831.
4.
AlamiM., FerriF., and GaslainY., Tetrahedron Lett., 1996, 37, 57.
5.
GrissonJ.W., GunawardenaG. U., KlingbergD., and HuangD., Tetrahedron, 1996, 52, 6453.
6.
NicolaouK.C., and DaiW. M., Angew. Chem., Int. Ed. Engl., 1991, 30, 1387.
7.
MiyauraN., YamadaK., SuginomeH., and SuzukiA., J. Am. Chem. Soc., 1985, 107, 972.
8.
NormantJ.F., CommerconA., and VillierasJ., Tetrahedron Lett., 1975, 1465.
9.
(a) RheeI., RyangM., and TsutsumiS., Tetrahedron Lett., 1969, 4593.
10.
AlexakisA., CahiezG., and NormantJ. F., Synthesis, 1979, 826.
11.
(a). KingA.O., OkukadoN., and NegishiE. I., J. Chem. Soc., Chem. Commun., 1977, 683.
12.
AbarbriM., ParrainJ. L., CintratJ. C., and DucheneA., Synthesis, 1996, 82.
13.
DangH.P., and LinstrumelleG., Tetrahedron Lett., 1978, 191.
14.
SheaR.G., FitznerJ. N., FankhauserJ. E., SpaltensteinA., CarpinoP. A., PeeveyR. M., PrattD. V., TengeB. J., and HopkinsP. B., J. Org. Chem., 1986, 51, 5243.
