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

Wang，Jiang1,3; Lin，Xin1,2; Shao，Pan Lin1,2; Song，Jingyuan1; Wen，Jialin1,4; Zhang，Xumu1

2021

10.1021/acscatal.1c03635

ACS Catalysis   影响因子和分区

2155-5435

2155-5435

This study presents an Rh/DuanPhos-catalyzed double asymmetric hydrogenation of α-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.

asymmetric hydrogenation DuanPhos stepwise transformation vicinal amino alcohols α-iminoketones

EI ; SCI

英语

第一 ; 通讯

Science, Technology and Innovation Commission of Shenzhen[JCYJ20190809160211372] ; National Natural Science Foundation of China[21991113] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Shenzhen Clean Energy Research Institute[CERI-KY-2019003]

Chemistry

Chemistry, Physical

WOS:000709692900029

AMER CHEMICAL SOC

20214311080044

Agricultural chemicals ; Reaction intermediates

Chemical Reactions:802.2 ; Chemical Products Generally:804 ; Agricultural Chemicals:821.2

2-s2.0-85117797414

Scopus

1.Shenzhen Grubbs Institute,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China
2.College of Innovation and Entrepreneurship,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China
3.School of Chemical Biology and Biotechnology,Peking University Shenzhen Graduate School,University Town,Shenzhen,Nanshan District,518055,China
4.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,1088 Xueyuan Road,518055,China

Wang，Jiang,Lin，Xin,Shao，Pan Lin,et al. Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols[J]. ACS Catalysis,2021,11(20):12729-12735.

Wang，Jiang,Lin，Xin,Shao，Pan Lin,Song，Jingyuan,Wen，Jialin,&Zhang，Xumu.(2021).Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols.ACS Catalysis,11(20),12729-12735.

Wang，Jiang,et al."Double Asymmetric Hydrogenation of α-Iminoketones: Facile Synthesis of Enantiopure Vicinal Amino Alcohols".ACS Catalysis 11.20(2021):12729-12735.