Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones
Simple Primary Amino Amide Organocatalyst for Enantioselective Aldol Reactions of Isatins with Ketones
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DOI：
10.1002/ejoc.201600414
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发表时间：
2016-08-01
影响因子：
2.8
通讯作者：
Nakano, Hiroto
中科院分区：
文献类型：
--
作者：
Kimura, Jo;Reddy, Ummareddy Venkata Subba;Nakano, Hiroto
发现使用新设计的氨基酰胺有机催化剂的各种靛红与酮的对映选择性羟醛缩合反应以良好至优异的产率和优异的立体选择性（高达99%，高达98%ee，顺/反= 99：1）提供手性3-取代的3-羟基-2-羟吲哚;一种催化剂3 i被证明特别成功。所得到的羟吲哚之一，3-羟基-3-（2-氧代环己基）-2-吲哚啉酮可以作为重要的药物化合物的合成中间体，并且本身显示出有趣的抗惊厥活性。
Enantioselective aldol reactions of various isatins with ketones using newly designed amino amide organocatalysts were found to provide chiral 3-substituted 3-hydroxy-2-oxindoles in good to excellent yields and with excellent stereoselectivities (up to 99 %, up to 98 % ee, syn/anti = 99: 1); one catalyst, 3i, proved particularly successful. One of the resulting oxindoles, 3-hydroxy-3-(2-oxocyclohexyl)-2-indolinone may serve as a synthetic intermediate for pharmaceutically important compounds and, in its own right, shows interesting anticonvulsant activities.