Enantioselective synthesis of indole-based unnatural β-Alkynyl α-amino acid derivatives via chiral phosphoric acid catalysis

被引：12

作者：

Woldegiorgis, Alemayehu Gashaw ^{[1
]}

Gu, Haorui ^{[1
]}

Lin, Xufeng ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

CHIRALITY | 2022年 / 34卷 / 04期

基金：

中国国家自然科学基金;

关键词：

artificial alpha-amino acids; chiral phosphoric acid; enantioselectivity; indole; organocatalysis; FRIEDEL-CRAFTS REACTION; ASYMMETRIC-SYNTHESIS; BEARING; CHEMISTRY; LIGANDS; BIOLOGY;

D O I：

10.1002/chir.23422

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The synthesis of unnatural alpha-amino acid derivatives has attracted considerable interest in recent years, as they are ubiquitous in protein synthesis and peptide-based drug discovery. Herein, we reported the chiral phosphoric acid catalyzed asymmetric reaction of indoles with beta,gamma-alkynyl-alpha-imino esters for the enantioselective synthesis of unnatural indole-based alpha-amino acid derivatives. This asymmetric organocatalysis protocol enables efficient synthesis of unnatural a-amino acid derivatives with a tetrasubstituted stereogenic center and an alkyne moiety with up to 99% yield and 98% ee, resulting in operationally simple conditions, short reaction time, and broad substrate scope.

引用

页码：678 / 693

页数：16

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