Catalytic enantioselective aldol reaction to ketones.
Catalytic enantioselective aldol reaction to ketones.
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DOI：
10.1021/ja061815w
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发表时间：
2006
影响因子：
15
通讯作者：
K. Oisaki;Dongbo Zhao;M. Kanai;M. Shibasaki
中科院分区：
文献类型：
--
作者：
K. Oisaki;Dongbo Zhao;M. Kanai;M. Shibasaki
以CuF-手性膦为催化剂，研究了酮与烯酮甲硅缩醛的不对称羟醛缩合反应。高对映体选择性的关键是开发一种新的衍生自Taniaphos的配体结合PhBF 3 K的独特的加速作用。这些条件适用于各种底物，如芳族、脂族和杂芳族酮。在取代的亲核试剂的情况下，反应进行得很好。的非对映选择性是独立的烯酮甲硅烷基缩醛的几何形状。这是使用烯酮甲硅烷基缩醛催化对映体和非对映体选择性羟醛缩合反应生成酮的第一个实例。
An enantioselective aldol reaction between ketones and ketene silyl acetals is described using CuF-chiral phosphine as a catalyst. The key for high enantioselectivity was the development of a novel ligand derived from Taniaphos combined with the unique accelerative effect of PhBF3K. These conditions are applicable to various substrates such as aromatic, aliphatic, and heteroaromatic ketones. In the case of substituted nucleophiles, the reaction proceeds well. The diastereoselectivity is independent of ketene silyl acetal geometry. This is the first example of a catalytic enantio- and diastereoselective aldol reaction to ketones using ketene silyl acetals.