用乙酰膦酸酯替代醋酸盐或乙酰胺作为有机催化的对映选择性羟醛反应的亲核试剂。
Acetylphosphonate as a surrogate of acetate or acetamide in organocatalyzed enantioselective aldol reactions.
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.
出版信息
Org Lett. 2012 Jun 15;14(12):3174-7. doi: 10.1021/ol301270w. Epub 2012 May 31.
Abstract
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.
摘要
手性奎宁衍生催化剂实现了乙酰膦酸酯和活性羰基化合物的高对映选择性羟醛反应，其中乙酰膦酸酯首次被直接用作烯醇化物前体。通过甲醇解或氨解，原位将得到的羟醛产物转化为相应的酯或酰胺。整个过程可以看作是形式上的高度对映选择性乙酸酯或乙酰胺羟醛反应，这是用有机催化方法很难直接实现的。
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