Platinum-Catalyzed Enantioselective Aldol Addition of Ketene Silyl Acetals to Aldehydes
Platinum-Catalyzed Enantioselective Aldol Addition of Ketene Silyl Acetals to Aldehydes
复制标题
铂催化烯酮甲硅烷基缩醛与醛的对映选择性羟醛加成
DOI：
10.1021/ja981970d
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发表时间：
1998
影响因子：
15
通讯作者：
Osamu Fujimura
中科院分区：
文献类型：
--
作者：
Osamu Fujimura
报道了第一个铂催化的对映选择性羟醛反应。该催化剂由手性双膦铂酰基配合物通过非配位或弱配位强酸活化生成，可用于催化烯酮甲硅烷基缩醛与各种醛的对映选择性羟醛加成。催化剂活化过程中需要氧气和水的存在才能获得对映选择性。在脂肪族伯醛的情况下观察到的对映选择性超过 90% 对映体过量。 IR 和 31P NMR 光谱用于证明 C 结合铂烯醇化物在醇醛缩合过程中的中间作用。
The first platinum-catalyzed enantioselective aldol reactions are reported. The catalysts are generated from chiral bisphosphine platinum acyl complexes by activation with noncoordinating or weakly coordinating strong acids and can be used to catalyze the enantioselective aldol addition of ketene silyl acetals to various aldehydes. The presence of oxygen and water during catalyst activation is required to obtain enantioselectivity. The enantioselectivities observed in the cases of aliphatic primary aldehydes are more than 90% enantiomer excess. IR and 31P NMR spectroscopies were used to demonstrate the intermediacy of C-bound platinum enolate in the aldol process.