Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols

被引：12
作者：
Wang, Jiang [1 ,2 ,3 ]
Lin, Xin [1 ,2 ,4 ]
Shao, Pan-Lin [1 ,2 ,4 ]
Song, Jingyuan [1 ,2 ]
Wen, Jialin [1 ,2 ,5 ]
Zhang, Xumu [1 ,2 ]
机构：
[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
[2] Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, Shenzhen 518055, Peoples R China
[3] Peking Univ, Sch Chem Biol & Biotechnol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[4] Southern Univ Sci & Technol, Coll Innovat & Entrepreneurship, Shenzhen 518055, Peoples R China
[5] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
来源：
ACS CATALYSIS | 2021年 / 11卷 / 20期
基金：
中国国家自然科学基金;
关键词：
asymmetric hydrogenation; DuanPhos; alpha-iminoketones; vicinal amino alcohols; stepwise transformation; CATALYZED ENANTIOSELECTIVE HYDROGENATION; KETONES; LIGANDS; IMINES; ROUTE; CONSTRUCTION; REAGENT; ACCESS; ESTERS;
D O I：
10.1021/acscatal.1c03635
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of alpha-iminoketones for accessing chiral vicinal amino alcohols, which are privileged motifs in pharmaceuticals, agrochemicals, fine chemicals, chiral auxiliaries, organocatalysts, etc. Compared with existing methods, this methodology has the following advantages, such as one-pot operation, high efficiency, operational simplicity, limited waste, broad reaction scope, and high yields (90 to 96%) and stereoselectivities (up to >99:1 dr; >99.9% ee). In addition, the mechanism of the transformation was revealed to be a stepwise reaction by isolating and analyzing reaction intermediates.
引用
收藏
页码：12729 / 12735
页数：7
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