Iwasawa Nobuharu, Miura Tomoya, Kiyota Koichi, Kusama Hiroyuki, Lee Kooyeon, Lee Phil Ho
Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Japan.
Org Lett. 2002 Dec 12;4(25):4463-6. doi: 10.1021/ol026993i.
[reaction: see text] A highly efficient method for the cyclopentene annulation onto alpha,beta-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto alpha,beta-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)(5)(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.
[反应：见正文] 描述了一种将环戊烯环化到α,β-不饱和酮上的高效方法。在叔丁基二甲基甲硅烷基三氟甲磺酸酯和二甲基硫醚存在下，铟介导的α,β-不饱和酮的1,4-炔丙基化反应生成6-硅氧基-5-烯-1-炔衍生物，该衍生物经W(CO)(5)(L)催化的5-内型-环化反应，以良好的产率得到相应的环戊烯衍生物。
