Simultaneous Access to Two Enantio-enriched Alcohols by a Single Ru-Catalyst: Asymmetric Hydrogen Transfer from Racemic Alcohols to Matching Ketones

Chen，Fumin1,2; Jin，Ming Yu2; Wang，David Zhigang3; Xu，Chen2; Wang，Jianchun2; Xing，Xiangyou2

2022-11-18

10.1021/acscatal.2c04657

ACS Catalysis   Impact Factor & Quartile

2155-5435

Oxidative kinetic resolution and asymmetric transfer hydrogenation are two classical methods to access chiral secondary alcohols. Described here is an example of cross asymmetric hydrogen transfer between H-donor racemic alcohols and H-acceptor prochiral ketones, which merge these two approaches in one catalytic cycle that could afford two chiral alcohols simultaneously. To create a large equilibrium constant for driving the reversible processes into completion, H-donor alcohols and H-acceptor ketones should have substituents with significantly different properties in sterics or electronics, yet this would cause a substantial challenge for a single catalyst to induce high ee's for both alcohols. Moreover, either enantiomer of a racemic alcohol could be obtained via sequential transfer hydrogenations with a single Ru-catalyst. These results collectively provide efficient access to two distinct enantio-enriched alcohols as well as both enantiomers of single alcohols.

cross asymmetric hydrogen transfer enantio-enriched alcohols equilibrium constant H-acceptor ketone Ru-catalyst

SCI

English

Corresponding

National Natural Science Foundation of China[K21211026];

WOS:000884840600001

2-s2.0-85141982014

Scopus

1.School of Chemistry and Chemical Engineering,Harbin Institute of Technology,Harbin,150001,China
2.Shenzhen Grubbs Institute and Department of Chemistry,Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China
3.Shenzhen Youwei Tech Group,Shenzhen,518057,China

Chen，Fumin,Jin，Ming Yu,Wang，David Zhigang,et al. Simultaneous Access to Two Enantio-enriched Alcohols by a Single Ru-Catalyst: Asymmetric Hydrogen Transfer from Racemic Alcohols to Matching Ketones[J]. ACS Catalysis,2022,12(22):14429-14435.

Chen，Fumin,Jin，Ming Yu,Wang，David Zhigang,Xu，Chen,Wang，Jianchun,&Xing，Xiangyou.(2022).Simultaneous Access to Two Enantio-enriched Alcohols by a Single Ru-Catalyst: Asymmetric Hydrogen Transfer from Racemic Alcohols to Matching Ketones.ACS Catalysis,12(22),14429-14435.

Chen，Fumin,et al."Simultaneous Access to Two Enantio-enriched Alcohols by a Single Ru-Catalyst: Asymmetric Hydrogen Transfer from Racemic Alcohols to Matching Ketones".ACS Catalysis 12.22(2022):14429-14435.