13657-14-2Relevant academic research and scientific papers
Enantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Br?nsted Acid Catalysis
Zhao, Feng,Shu, Chang,Young, Claire M.,Carpenter-Warren, Cameron,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 11892 - 11900 (2021/04/28)
The synthesis of α-aryl-β2-amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Br?nsted acid catalysis is demonstrated. The scope and limitatio
One-Pot Synthesis of α-Halo β-Amino Acid Derivatives via the Difunctional Coupling of Ethyl α-Diazoacetate with Silyl Halides and N, O -Acetals or Aromatic Tertiary Amines
Ogiwara, Yohei,Sakai, Norio,Sasaki, Kazuki,Suzuki, Hiroki
supporting information, p. 1823 - 1832 (2020/06/08)
The difunctionalization of ethyl α-diazoacetate (EDA) using silyl halides as a nucleophile and N, O -acetals as an electrophile under metal-free conditions is described. This process undergoes a novel three-component coupling (3-CC) reaction using EDA, which leads to a one-pot preparation of α-halo β-amino acid esters. Also, this protocol could be adapted to accept an electrophile composed of aromatic tertiary amines. In both 3-CC reactions, the key reaction intermediate is an iminium intermediate that can be easily and effectively generated either from N, O -acetals or from aromatic tertiary amines.
Copper-Catalyzed Oxy-aminomethylation of Diazo Compounds with N, O-Acetals
Yu, Jianliang,Chen, Long,Sun, Jiangtao
supporting information, p. 1664 - 1667 (2019/03/11)
A novel oxy-aminomethylation reaction of diazo compounds has been developed, providing the α-hydroxy-β2-amino acid derivatives with quaternary carbon centers in moderate to excellent yields. Importantly, the readily available N,O-acetals have been employed as efficient bifunctionalization reagents to react with copper carbene intermediates, leading to the concurrent incorporation of an alkoxy and an iminium group into one molecule. Moreover, a water-involved three-component reaction occurs to deliver the free-hydroxy amino acid derivatives.
Hf(OTf)4-Catalyzed regioselective N -aminomethylation of indoles and related NH-containing heterocycles
Sakai, Norio,Shimamura, Kazuyori,Ikeda, Reiko,Konakahara, Takeo
supporting information; experimental part, p. 3923 - 3926 (2010/07/05)
Figure presented Under Lewis acidic conditions using Hf(OTf)4, the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.
