Enantioselective Friedel-Crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent
Enantioselective Friedel-Crafts alkylations with benzoylhydrazones promoted by a simple strained silacycle reagent
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DOI：
10.1021/ja042522a
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发表时间：
2005-03-09
影响因子：
15
通讯作者：
Leighton, JL
中科院分区：
文献类型：
--
作者：
Shirakawa, S;Berger, R;Leighton, JL
描述了富电子芳烃和杂芳烃在单手性硅烷Lewis酸介导下与乙醛异丙酯苯甲酰腙的对映选择性Friedel−Crafts反应。在更大规模（5 g的腙）反应中，伪麻黄碱的回收率达到99%，证明了该反应具有很高的实用性。提出了一个简单的模型来解释观察到的对映体选择性。
The enantioselective Friedel−Crafts reaction of electron-rich arenes and heteroarenes with the benzoylhydrazone of isopropyl glyoxylate mediated by a simple chiral silane Lewis acid is described. The reactions are highly practical, as demonstrated by a larger scale (5 g of the hydrazone) reaction in which the recovery of the pseudoephedrine in 99% yield was achieved. A simple model is advanced to explain the observed enantioselectivity.