122394-38-1Relevant articles and documents
An efficient synthesis of aryl α-keto esters
Ma, Ming,Li, Changkun,Peng, Lingling,Xie, Fang,Zhang, Xiu,Wang, Jianbo
, p. 3927 - 3929 (2005)
A new one-pot approach for the synthesis of aryl α-keto ester based on the diazo transfer and oxidation of diazo group is developed.
Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones
Liu, Yonggui,Luo, Guoyong,Yang, Xing,Jiang, Shichun,Xue, Wei,Chi, Yonggui Robin,Jin, Zhichao
supporting information, p. 442 - 448 (2019/11/25)
The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.
Enantioselective Iridium-Catalyzed Hydrogenation of α-Keto Amides to α-Hydroxy Amides
Gu, Guoxian,Yang, Tilong,Yu, Ouran,Qian, Hua,Wang, Jiang,Wen, Jialin,Dang, Li,Zhang, Xumu
supporting information, p. 5920 - 5923 (2017/11/10)
A highly enantioselective iridium-catalyzed hydrogenation of α-keto amides to form α-hydroxy amides has been achieved with excellent results (up to >99% conversion and up to >99% ee, TON up to 100?000). As an example, this protocol was applied to the synthesis of (S)-4-(2-amino-1-hydroxyethyl)benzene-1,2-diol, the enantiomer of norepinephrine, which is widely used as an injectable drug for the treatment of critically low blood pressure. Density functional theory (DFT) calculations were also carried out to reveal the reaction mechanism.