No electron-withdrawing or electron-releasing substituents are necessary for the substrates in the rhodium-catalyzed [4+2] cycloaddition reaction between a vinylallene and an ordinary alkyne under mild conditions [Eq. (1)]. The use of the strongly electron-accepting P[OCH(CF3 )2 ]3 ligand affords the optimal rhodium catalyst. cod = 1,5-cyclooctadiene.
Holm, Kjetil H.; Skatteboel, Lars, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1984, vol. 38, # 9, p. 783 - 794
作者:Holm, Kjetil H.、Skatteboel, Lars
DOI:——
日期:——
Directed Intermolecular [4 + 2] Cycloaddition of Unactivated 1,3-Diene Substrates with High Regio- and Stereoselectivities
作者:Masahiro Murakami、Kenichiro Itami、Yoshihiko Ito
DOI:10.1021/ja970626y
日期:1997.7.1
Construction of Eight-Membered Carbocycles by Palladium-Catalyzed [4 + 4] Cycloaddition of Vinylallenes
作者:Masahiro Murakami、Kenichiro Itami、Yoshihiko Ito
DOI:10.1055/s-1999-3087
日期:——
A palladium-catalyzed [4 + 4] cycloaddition reaction is described. A vinylallene having a pendant phenyl or vinyl substituent was treated with a catalytic amount of a palladium(O) complex to afford a symmetrical eight-membered carbocycle. The extended conjugation of the diene unit of an intermediate with the pendant unsaturated substituent is important for the [4 + 4] cycloaddition to occur.