Highly efficient and enantioselective synthesis of β-heteroaryl amino alcohols via Ru-catalyzed asymmetric hydrogenation

Wu，Chao1,2; Ma，Baode2; Chen，Gen Qiang3; Zhang，Xumu2,4

2022-10-13

10.1039/d2cc03701g

CHEMICAL COMMUNICATIONS   Impact Factor & Quartile

1359-7345

1364-548X

Chiral β-heteroaryl amino alcohols are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective hydrogenation of α-N-heteroaryl ketones was realized with a ruthenium-diphosphine-diamine catalyst, providing the corresponding chiral β-heteroaryl amino alcohols with up to 99% yield and up to >99% ee. The synthetic utilities of the current reaction were demonstrated by gram-scale synthesis of key intermediates of Sertaconazole and Cenobamate.

SCI

English

NI Journal Papers

Corresponding

National Key R&D Program of China[2021YFA1500201] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002] ; Shenzhen Science and Technology Innovation Committee[JCYJ20210324104202007] ; National Natural Science Foundation of China["22001113","21901107","22171129"] ; Stable Support Plan Program of Shenzhen Natural Science Fund[20200925161222002] ; Guangdong Basic and Applied Basic Research Foundation[2022B1515020055]

Chemistry

Chemistry, Multidisciplinary

WOS:000874485200001

ROYAL SOC CHEMISTRY

CHEMISTRY

2-s2.0-85141510263

Scopus

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China
2.Shenzhen Grubbs Institute,Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
3.Academy for Advanced Interdisciplinary Studies,Southern University of Science and Technology,Shenzhen,518000,China
4.Shenzhen Bay Laboratory,Shenzhen,518132,China

Wu，Chao,Ma，Baode,Chen，Gen Qiang,et al. Highly efficient and enantioselective synthesis of β-heteroaryl amino alcohols via Ru-catalyzed asymmetric hydrogenation[J]. CHEMICAL COMMUNICATIONS,2022,31(17-19).

Wu，Chao,Ma，Baode,Chen，Gen Qiang,&Zhang，Xumu.(2022).Highly efficient and enantioselective synthesis of β-heteroaryl amino alcohols via Ru-catalyzed asymmetric hydrogenation.CHEMICAL COMMUNICATIONS,31(17-19).

Wu，Chao,et al."Highly efficient and enantioselective synthesis of β-heteroaryl amino alcohols via Ru-catalyzed asymmetric hydrogenation".CHEMICAL COMMUNICATIONS 31.17-19(2022).