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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
Synthesis ( IF 2.2 ) Pub Date : 2020-03-23 , DOI: 10.1055/s-0039-1690864
Norio Sakai , Kazuki Sasaki , Hiroki Suzuki , Yohei Ogiwara

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.

中文翻译:

通过α-重氮乙酸乙酯与硅烷基卤化物和N,O-缩醛或芳族叔胺的双官能团偶联合成α-卤代β-氨基酸衍生物

描述了在无金属条件下使用甲硅烷基卤化物作为亲核试剂和NO-乙缩醛作为亲电试剂对α-重氮乙酸乙酯(EDA)进行双官能化的方法。此过程使用EDA进行了新颖的三组分偶联(3-CC)反应,从而制备了一锅的α-卤代β-氨基酸酯。同样,该协议可适于接受由芳族叔胺组成的亲电试剂。在这两个3-CC反应中,关键的反应中间体是亚胺中间体,可以轻松,有效地从NO-乙缩醛或芳族叔胺中生成。
更新日期:2020-03-23
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