Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.
Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.
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DOI：
10.1021/ol301270w
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发表时间：
2012-06-15
期刊：
影响因子：
5.2
通讯作者：
Zhao, John Cong-Gui
中科院分区：
文献类型：
--
作者：
Guang, Jie;Guo, Qunsheng;Zhao, John Cong-Gui
首次以乙酰膦酸酯为烯醇化物前体，在金鸡纳生物碱衍生物催化下实现了乙酰膦酸酯与活化羰基化合物的高对映选择性羟醛缩合反应。所得羟醛产物通过甲醇解或氨解原位转化为相应的酯或酰胺。整个过程可以被看作是形式上的高度对映选择性的乙酸酯或乙酰胺羟醛缩合反应，这是非常难以直接用有机催化方法实现的。
Highly enantioselective aldol reactions of acetylphosphonates and activated carbonyl compounds was realized with cinchona alkaloid derived catalysts, in which the acetylphosphonate was directly used as an enolate precursor for the first time. The aldol product obtained was converted in situ to its corresponding ester or amide through methanolysis or aminolysis. The overall process may be viewed as formal highly enantioselective acetate or acetamide aldol reactions, which are very difficult to achieve directly with organocatalytic methods.
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