Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
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DOI：
10.1021/ja304095z
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发表时间：
2012-06-27
影响因子：
15
通讯作者：
Masson, Geraldine
中科院分区：
文献类型：
--
作者：
Alix, Aurelien;Lalli, Claudia;Masson, Geraldine
不含金属的手性磷酸和手性磷酸钙都催化烯氨基甲酸酯的高度对映和非对映选择性的亲电α-溴化反应，以提供对映富集的邻位卤胺的原子经济的合成。通过简单地将催化剂从磷酸切换到其钙盐，可以以良好的产率以优异的非对映体和对映体选择性形成任一对映体。
Metal-free chiral phosphoric acids and chiral calcium phosphates both catalyze highly enantio- and diastereoselective electrophilic alpha-bromination of enecarbamates to provide an atom-economical synthesis of enantioenriched vicinal haloamines. Either enantiomer can be formed in good yield with excellent diastereo- and enantioselectivity simply by switching the catalyst from a phosphoric acid to its calcium salt.