Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β‐Ketonitrile Derivatives |
| |
| Authors: | Dr Kensuke Kiyokawa Takaya Nagata Prof Dr Satoshi Minakata |
| |
| Institution: | Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka, Japan |
| |
| Abstract: | The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N‐cyano‐N‐phenyl‐p‐toluenesulfonamide (NCTS) and p‐toluenesulfonyl cyanide (TsCN), is reported. Various β‐ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of β‐ketonitriles containing a quaternary α‐carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described. |
| |
| Keywords: | boron cyanation nucleophilic addition reaction mechanisms synthetic methods |
|
|
