Electrostatic Repulsion and Hydrogen‐Bonding Interactions in a Simple N‐Aryl‐L‐valinamide Organocatalyst Control the Stereoselectivity in Asymmetric Aldol Reactions
Electrostatic Repulsion and Hydrogen‐Bonding Interactions in a Simple N‐Aryl‐L‐valinamide Organocatalyst Control the Stereoselectivity in Asymmetric Aldol Reactions
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DOI：
10.1002/ejoc.201301138
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发表时间：
2013-10
影响因子：
2.8
通讯作者：
Yuya Tanimura;K. Yasunaga;K. Ishimaru
中科院分区：
文献类型：
--
作者：
Yuya Tanimura;K. Yasunaga;K. Ishimaru
描述了一种新的醛与酮的不对称Aldol反应的立体控制方法。产物的立体选择性受N-芳基-L-缬氨酰胺催化剂的静电斥力和氢键相互作用控制。在交叉羟醛反应中使用该催化剂可以很容易地获得生物活性的3-环己酮-3-羟基-2-氧吲哚，具有良好的非对映-(syn/anti=>；99：1)和对映体选择性(>；99%ee)。
A novel stereocontrol method for asymmetric aldol reactions of aldehydes with ketones is described. The stereoselectivity of the products is controlled by the electrostatic repulsion and hydrogen-bonding interactions of an N-aryl-L-valinamide catalyst. The use of this catalyst in a cross-aldol reaction allows easy access to bioactive 3-cyclohexanone-3-hydroxy-2-oxindole with excellent diastereo- (syn/anti = >99:1) and enantioselectivity (>99 % ee).