4.8 Article

Nickel/Copper-Cocatalyzed Asymmetric Benzylation of Aldimine Esters for the Enantioselective Synthesis of α-Quaternary Amino Acids

期刊

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202203448

关键词

Amino Acids; Asymmetric Catalysis; Benzylation; Bimetallic Catalysis; Earth-Abundant Metal

资金

  1. NSFC [21831005, 21901158, 21991112, 22171183]
  2. National Key R&D Program of China [2018YFE0126800]
  3. Shanghai Sailing Program [19YF1421900]

向作者/读者索取更多资源

The first asymmetric Ni/Cu cocatalyzed benzylation of aldimine esters is reported, allowing the synthesis of benzyl-substituted alpha-quaternary amino acids in high yield and with high enantioselectivity. The strong electrophilicity of the eta(3)-benzylnickel intermediate was found to be crucial for the high reactivity, enabling the reaction under base-free conditions.
The first asymmetric Ni/Cu cocatalyzed benzylation of aldimine esters is reported. A series of benzyl-substituted alpha-quaternary amino acids could be synthesized in high yield and with high levels of enantioselectivity (up to 90 % yield and 99 % ee). The experimental and theoretical calculation results suggested that the strong electrophilicity of the eta(3)-benzylnickel intermediate is crucial for the high reactivity, enabling the reaction under base-free conditions. Furthermore, this method has been applied to the synthesis of the cell adhesion inhibitor BIRT-377 analogues, and the key intermediate of the NK1 receptor antagonist PD154075 and CCK-B receptor antagonist CI-988.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据