一种用于在α,β-不饱和酮上进行环化的新型反应：W(CO)₅.L促进了通过丙炔基丙二酸酯与烯酮的1,4-加成制备的ω-炔丙基甲硅烷基烯醇醚的外型和内型选择性环化反应。
A novel reaction for annulation onto alpha,beta-unsaturated ketones: W(CO)(5).L promoted exo- and endo-selective cyclizations of omega-acetylenic silyl enol ethers prepared by 1,4-addition of propargyl malonate to enones.
作者信息
Iwasawa N, Maeyama K, Kusama H
机构信息
Department of Chemistry, Tokyo Institute of Technology, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
出版信息
Org Lett. 2001 Nov 29;3(24):3871-3. doi: 10.1021/ol016718g.
A highly useful method for five- and six-membered ring annulation onto alpha,beta-unsaturated ketones is described. 1,4-Addition of propargylmalonate to alpha,beta-unsaturated ketones in the presence of silyl triflate gives 7-siloxy-6-en-1-yne derivatives in good yield. W(CO)(5).L-catalyzed cyclization of these substrates can be induced to give preferentially either exo- or endo-cyclized products in good yield simply by changing the reaction solvent. [reaction: see text]
描述了一种在α,β-不饱和酮上进行五元环和六元环环化的非常有用的方法。在三氟甲磺酸硅存在下，丙炔基丙二酸酯与α,β-不饱和酮进行1,4-加成反应，以良好的产率得到7-硅氧基-6-烯-1-炔衍生物。通过简单地改变反应溶剂，W(CO)₅·L催化这些底物的环化反应可以优先得到产率良好的外型或内型环化产物。[反应：见正文]
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