铟介导的在2-氮杂环丁酮的C4位选择性引入1,3-丁二烯-2-基以及1,3-二烯连接的2-氮杂环丁酮在狄尔斯-阿尔德反应中的应用。
Indium-mediated selective introduction of a 1,3-butadien-2-yl group at the C4-position in 2-azetidinones and application of 1,3-diene-tethered 2-azetidinones in the Diels-Alder reaction.
作者信息
Lee Kooyeon, Lee Phil Ho
机构信息
National Research Laboratory of Catalytic Organic Reaction, Department of Chemistry and Institute for Basic Science, Kangwon National University, Chunchon 200-701, Republic of Korea.
出版信息
Chemistry. 2007;13(31):8877-83. doi: 10.1002/chem.200700796.
The reaction of 4-acetoxy-2-azetidinones with organoindium reagents generated in situ from indium and 1,4-dibromo-2-butyne in the presence of LiCl in DMF selectively produced 2-azetidinones which contain a 1,3-butadienyl-2-yl group at the C4-position in good yields. The Diels-Alder reaction of 4-[(1-methylene)prop-2-enyl]-2-azetidinones with a variety of dienophiles provided 2-azetidinones with valuable functional-group-substituted six-membered rings at the C4-position in good yields.
在DMF中，4-乙酰氧基-2-氮杂环丁酮与由铟和1,4-二溴-2-丁炔在LiCl存在下原位生成的有机铟试剂反应，选择性地高产率生成在C4位含有1,3-丁二烯-2-基的2-氮杂环丁酮。4-[(1-亚甲基)丙-2-烯基]-2-氮杂环丁酮与多种亲双烯体的狄尔斯-阿尔德反应高产率地提供了在C4位具有有价值的官能团取代六元环的2-氮杂环丁酮。
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