7391-32-4Relevant academic research and scientific papers
Asymmetric Transfer Hydrogenation of α-Substituted-β-Keto Carbonitriles via Dynamic Kinetic Resolution
Wang, Fangyuan,Yang, Tilong,Wu, Ting,Zheng, Long-Sheng,Yin, Congcong,Shi, Yongjie,Ye, Xiang-Yu,Chen, Gen-Qiang,Zhang, Xumu
supporting information, p. 2477 - 2483 (2021/02/16)
A catalytic protocol for the enantio- and diastereoselective reduction of α-substituted-β-keto carbonitriles is described. The reaction involves a DKR-ATH process with the simultaneous construction of β-hydroxy carbonitrile scaffolds with two contiguous stereogenic centers. A wide range of α-substituted-β-keto carbonitriles were obtained in high yields (94%-98%) and excellent enantio- and diastereoselectivities (up to >99% ee, up to >99:1 dr). The origin of the diastereoselectivity was also rationalized by DFT calculations. Furthermore, this methodology offers rapid access to the pharmaceutical intermediates of Ipenoxazone and Tapentadol.
Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives
Kiyokawa, Kensuke,Nagata, Takaya,Minakata, Satoshi
supporting information, p. 10458 - 10462 (2016/08/24)
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.
