Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers
Aromatic aldehyde-selective aldol addition with aldehyde-derived silyl enol ethers
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DOI：
10.1039/c7cc08936h
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发表时间：
2018-01-14
影响因子：
4.9
通讯作者：
Sawama, Yoshinari
中科院分区：
文献类型：
--
作者：
Kawajiri, Takahiro;Ohta, Reiya;Sawama, Yoshinari
在三氟甲磺酸甲硅酯和2，2 '-联吡啶存在下，以三氟甲磺酸甲硅酯衍生的烯醇化甲硅酯为亲核试剂，与芳香醛进行化学选择性的羟醛缩合反应，生成β-甲硅烷氧基醛，而脂肪醛完全回收。前所未有的化学选择性取决于衍生自芳香族和脂肪族醛的吡啶鎓型中间体的反应性。
The aldol reaction using aldehyde-derived silyl enolates as nucleophiles with aromatic aldehydes chemoselectively proceeded in the presence of silyl triflate and 2,2'-bipyridyl to produce beta-siloxy aldehydes, while the aliphatic aldehydes were completely recovered. The unprecedented chemoselectivities depend on the reactivities of the pyridinium-type intermediates derived from the aromatic and aliphatic aldehydes.