Taguchi Takeo, Saito Akio, Yanai Hikaru
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1423-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
Chem Rec. 2007;7(3):167-79. doi: 10.1002/tcr.20112.
We have developed novel bidentate Lewis acids that efficiently promote the intramolecular cycloaddition reactions of ester-tethered substrates. Bis-aluminated triflic amide derivatives [TfN(AlR(1)R(2))2], which are generated by simply mixing triflic amide and 2 equiv of methyl aluminum or aluminum hydride, catalyzed intramolecular Diels-Alder (DA) reactions of ester-tethered 1,7,9-trienes and intermolecular DA reactions of alpha,beta-unsaturated lactones. We also found that bimetallic Lewis acid derived from 1,1'-biphenyl-2,2'-di(triflyl)amide and dimethylaluminum chloride promoted the intramolecular [3 + 2] cycloaddition reaction of acrylate derivatives having an allylsilane part.
我们已经开发出新型双齿路易斯酸，其能有效促进酯连接底物的分子内环加成反应。双铝化三氟甲磺酰胺衍生物[TfN(AlR(1)R(2))2]，通过简单混合三氟甲磺酰胺和2当量的甲基铝或氢化铝生成，催化酯连接的1,7,9 - 三烯的分子内狄尔斯 - 阿尔德（DA）反应以及α,β - 不饱和内酯的分子间DA反应。我们还发现，由1,1'-联苯 - 2,2'-二（三氟甲磺酰）酰胺和二甲基氯化铝衍生的双金属路易斯酸促进了具有烯丙基硅烷部分的丙烯酸酯衍生物的分子内[3 + 2]环加成反应。
