Conjugate Addition-Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis

被引：253

作者：

Yin, Yanli ^{[1
,2
]}

Dai, Yating ^{[1
]}

Jia, Hongshao ^{[1
]}

Li, Jiangtao ^{[1
]}

Bu, Liwei ^{[1
]}

Qiao, Baokun ^{[1
]}

Zhao, Xiaowei ^{[1
]}

Jiang, Zhiyong ^{[1
]}

机构：

[1] Henan Univ, Key Lab Nat Med & Immunoengn, Kaifeng 475004, Henan, Peoples R China

[2] Henan Univ Technol, Coll Bioengn, Zhengzhou 450001, Henan, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 19期

关键词：

OPTICALLY-ACTIVE PHENIRAMINE; CARBOXYLIC-ACIDS; AMINO RADICALS; DECARBOXYLATIVE ARYLATION; ACTIVATING GROUPS; BRONSTED ACID; HYDROGENATION; FUNCTIONALIZATION; ALKYLATION; DIASTEREO;

D O I：

10.1021/jacs.8b01575

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective protonation strategy has been successfully applied to the synthesis of chiral a-tertiary azaarenes. With a dual catalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer that is mediated by visible light, a variety of a-branched 2-vinylpyridines and 2-vinylquinolines with N-aryl glycines underwent a redox-neutral, radical conjugate addition-protonation process and provided valuable chiral 3-(2-pyridine/quinoline)-3-substituted amines in high yields with good to excellent enantioselectivities (up to >99% ee). An application of this methodology to a two-step synthesis of the enantiomerically pure medicinal compound pheniramine (Avil) is also presented.

引用

页码：6083 / 6087

页数：5