Kinetic Resolution of Azaarylethynyl Tertiary Alcohols by Chiral Bronsted Acid Catalysed Phosphine-Mediated Deoxygenation

被引：13

作者：

Wang, Guanghui ^{[1
]}

Li, Lulu ^{[1
]}

Jiang, Yifeng ^{[1
]}

Zhao, Xiaowei ^{[2
]}

Ban, Xu ^{[1
]}

Shao, Tianju ^{[1
]}

Yin, Yanli ^{[1
,3
]}

Jiang, Zhiyong ^{[1
,2
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

[2] Henan Univ, Int Sci & Technol Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China

[3] Henan Univ Technol, Coll Adv Interdisciplinary Sci & Technol, Zhengzhou 450001, Henan, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 04期

基金：

中国博士后科学基金;

关键词：

Allenes; Azaarenes; Chiral Bronsted Acid Catalysis; Kinetic Resolution; Propargylic Tertiary Alcohols; EFFICIENT SYNTHESIS; HIGHLY EFFICIENT; NUCLEOPHILES; DIASTEREO; ADDITIONS; FUNCTIONALIZATION; ALKYLATIONS; COMPLEXES; STRATEGY; ALLENES;

D O I：

10.1002/anie.202214838

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A chiral Bronsted acid catalysed phosphine-mediated deoxygenation protocol is reported. This metal-free method provides a precise kinetic resolution platform for azaarylethynyl tertiary alcohols, which are a broad category of biologically and synthetically important azaarene derivatives. In addition to providing an efficient method for the first asymmetric preparation of these tertiary alcohols, the strategy facilitates the construction of azaaryl-functionalized allenes with good to excellent enantioselectivities. The high selectivity factors (s up to 235), broad substrate scope, and ability to convert azaaryl compounds into both chiral tertiary alcohols and allenes robustly underscore the efficiency and promising utility of this method. The practicability is further validated by the successful synthesis of deuterated allenes with high ee values and substantial incorporation of deuterium using inexpensive D2O as the deuterium source.

引用

页数：6

共 43 条

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