Azuma Takumi, Takemoto Yoshiji, Takasu Kiyosei
Graduate School of Pharmaceutical Sciences, Kyoto University, Japan.
Chem Pharm Bull (Tokyo). 2011;59(9):1190-3. doi: 10.1248/cpb.59.1190.
We describe here a Tf₂NH-catalyzed formal (3+3) cycloaddition of silyl enol ethers with acrylates as a new domino reaction. In the domino sequence, the catalyst activates Michael addition, deprotonation of the resulting silyloxonium cation and intramolecular Claisen condensation. It was found that reaction modes significantly depend on the reaction temperature. We also examined the mechanistic detail of the reaction by ¹H-NMR experiment.
我们在此描述一种由双（三氟甲磺酰）亚胺催化的硅烯醇醚与丙烯酸酯的形式上的（3+3）环加成反应，这是一种新的多米诺反应。在多米诺反应序列中，催化剂激活迈克尔加成反应、所得硅鎓阳离子的去质子化反应以及分子内克莱森缩合反应。研究发现，反应模式显著取决于反应温度。我们还通过¹H-NMR实验研究了该反应的机理细节。
