Trost Barry M, Yang Hanbiao, Wuitschik Georg
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Org Lett. 2005 Oct 13;7(21):4761-4. doi: 10.1021/ol0520065.
[reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran.
[反应：见正文] 报道了一种钌催化的串联炔烃-烯酮偶联/迈克尔加成反应。该反应提供了一种高效、原子经济的方法，可从简单易得的高炔丙醇和β,γ-不饱和烯酮以良好的产率制备4-亚甲基-2,6-顺式四氢吡喃。所得乙烯基硅烷的进一步官能化导致合成2,6-顺式二氢吡喃环外几何构型确定的三取代烯烃。
