Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

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• 作者：Yoshizumi Yasui ; Haruhi Kamisaki ; Takayuki Ishida ; Yoshiji Takemoto
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：13 March 2010
• 年：2010
• 卷：66
• 期：11
• 页码：1980-1989
• 全文大小：818 K

文摘

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 °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.