Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
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DOI：
10.1016/j.tet.2010.01.073
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发表时间：
2010-03-13
期刊：
影响因子：
2.1
通讯作者：
Takemoto, Yoshiji
中科院分区：
文献类型：
--
作者：
Yasui, Yoshizumi;Kamisaki, Haruhi;Takemoto, Yoshiji
实现了烯烃的氰酰胺化。当N-(2-乙烯基苯基)氰基甲酰胺用钯催化剂处理时，发生分子内氰酰胺化，得到相应的3,3-二取代的羟吲哚。 P(t-Bu)(3)对此反应表现出显着的效果。当它与 Pd(dba)(2) 一起使用时，许多底物的反应在 100 摄氏度下 15 分钟内完成。此外，用Pd(dba)(2)和光学活性亚磷酰胺完成对映选择性氰酰胺化，得到光学活性3,3-二取代的羟吲哚。已经研究了所产生的羟吲哚的操纵。 (C) 2010 Elsevier Ltd. 保留所有权利。
The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.