Further studies on palladium-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3
摘要:
Bismetallative cyclization of enynes with Bu3SnSiMe3 catalyzed by Pd(0) complex was realized for the first time, which gives cyclized products containing a vinylsilane moiety and a homoallyltin moiety in good yield. In this cyclization, Pd-2(dba)(3)(CHCl3)-C-. or Pd(OH)2 on charcoal is effective as a Pd(0) catalyst and the addition of a phosphine ligand increased the formation of alkyne bismetallation by-product. On the other hand, it was found that a nucleophilic N-heterocyclic carbene could be utilized as a ligand for this cyclization. The utility of the cyclized products obtained from this cyclization in synthetic organic chemistry have been proven by transformation into cyclopropanol derivatives. (C) 2003 Elsevier B.V. All rights reserved.
Palladium-Catalyzed Bismetallative Cyclization of Enynes
作者:Miwako Mori、Tomohiro Hirose、Hideaki Wakamatsu、Noriko Imakuni、Yoshihiro Sato
DOI:10.1021/om000979x
日期:2001.5.1
Enynes were reacted with Me3SiSnBu3 in the presence of Pd(2)dba(3). CHCl3 or Pd(OH)(2) on charcoal to give cyclized products containing a vinylsilane moiety and a homoallyltin moiety in good yield.
Further studies on palladium-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3
作者:Yoshihiro Sato、Noriko Imakuni、Tomohiro Hirose、Hideaki Wakamatsu、Miwako Mori
DOI:10.1016/s0022-328x(03)00601-6
日期:2003.12
Bismetallative cyclization of enynes with Bu3SnSiMe3 catalyzed by Pd(0) complex was realized for the first time, which gives cyclized products containing a vinylsilane moiety and a homoallyltin moiety in good yield. In this cyclization, Pd-2(dba)(3)(CHCl3)-C-. or Pd(OH)2 on charcoal is effective as a Pd(0) catalyst and the addition of a phosphine ligand increased the formation of alkyne bismetallation by-product. On the other hand, it was found that a nucleophilic N-heterocyclic carbene could be utilized as a ligand for this cyclization. The utility of the cyclized products obtained from this cyclization in synthetic organic chemistry have been proven by transformation into cyclopropanol derivatives. (C) 2003 Elsevier B.V. All rights reserved.