Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens

被引：32

作者：

Yang, Peng ^{[1
]}

Sun, Yaxin ^{[1
]}

Fu, Kaiyue ^{[1
]}

Zhang, Li ^{[1
]}

Yang, Guang ^{[1
]}

Yue, Jieyu ^{[1
]}

Ma, Yu ^{[1
]}

Zhou, Jianrong Steve ^{[2
]}

Tang, Bo ^{[1
]}

机构：

[1] Shandong Normal Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Mol & Nano Probes, Minist Educ,Collaborat Innovat Ctr Functionalized, Jinan 250014, Peoples R China

[2] Peking Univ Shenzhen Grad Sch, State Key Lab Chem Oncogen, Key Lab Chem Genom, Sch Chem Biol & Biotechnol, Room F312 2199 Lishui Rd, Shenzhen 518055, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 01期

基金：

中国国家自然科学基金;

关键词：

cascade reaction; chiral carboxylic acid; hydrocarboxylation; Nickel; transfer hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; SUBSTITUTED ACRYLIC-ACIDS; REGIOSELECTIVE HYDROCARBOXYLATION; STEREOSELECTIVE HYDROCARBOXYLATION; TERMINAL ALKYNES; CARBON-DIOXIDE; LIGANDS; OLEFINS; ARYL; PD;

D O I：

10.1002/anie.202111778

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We report a stereoselective conversion of terminal alkynes to alpha-chiral carboxylic acids using a nickel-catalyzed domino hydrocarboxylation-transfer hydrogenation reaction. A simple nickel/BenzP* catalyst displayed high activity in both steps of regioselective hydrocarboxylation of alkynes and subsequent asymmetric transfer hydrogenation. The reaction was successfully applied in enantioselective preparation of three nonsteroidal anti-inflammatory profens (>90 % ees) and the chiral fragment of AZD2716.

引用

页数：5

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