Synthesis of Chiral Homoallylic Nitriles by Iridium-Catalyzed Allylation of Cyanoacetates

Synthesis of Chiral Homoallylic Nitriles by Iridium-Catalyzed Allylation of Cyanoacetates

A synthesis of chiral homoallylic nitriles by the iridium-catalyzed allylation of cyanoacetates followed by Krapcho demethoxycarbonylation has been developed. A wide range of homoallylic nitriles were obtained with a high enantioselectivity (>95–99% ee). These compounds are useful chiral building...

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Veröffentlicht in:Journal of organic chemistry 2018-10, Vol.83 (19), p.12239-12246
Hauptverfasser: Matsunami, Asuka, Takizawa, Kazuki, Sugano, Shogo, Yano, Yusuke, Sato, Hiroaki, Takeuchi, Ryo
Format: Artikel
Sprache:eng
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Zusammenfassung:A synthesis of chiral homoallylic nitriles by the iridium-catalyzed allylation of cyanoacetates followed by Krapcho demethoxycarbonylation has been developed. A wide range of homoallylic nitriles were obtained with a high enantioselectivity (>95–99% ee). These compounds are useful chiral building blocks because further synthetic elaboration starting from a nitrile or terminal alkene is possible.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01632