Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation |
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| Authors: | Yoshizumi Yasui Takayuki Ishida |
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| Institution: | a World Premier International Research Center, Advanced Institute for Materials Research, Tohoku University, Aoba, Sendai 980-8578, Japan
b Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan |
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| Abstract: | 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. |
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