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Synfacts 2019; 15(12): 1381
DOI: 10.1055/s-0039-1691254
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Preparation of Chiral Hydrazines

Rezensent(en):
Paul Knochel
,
Alexander Kremsmair
Hu Y, Zhang Z, Zhang J, Liu Y, Gridnev ID, Zhang W. * Shanghai Jiao Tong University, P. R. of China
Cobalt-Catalyzed Asymmetric Hydrogenation of C=N Bonds Enabled by Assisted Coordination and Nonbonding Interactions.

Angew. Chem. Int. Ed. 2019;
58: 15767-15771
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Publikationsverlauf

Publikationsdatum:
18. November 2019 (online)

 
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Key words

asymmetric hydrogenation - chiral amines - cobalt catalysis - hydrazines - hydrazones

Significance

Zhang and co-workers developed a cobalt-catalyzed hydrogenation of substituted hydrazones, which leads to chiral hydrazines in excellent yield and enantioselectivity. Further functionalization of the hydrozines leads to synthetically useful amines, amides, and pyrazole derivatives.


 

Comment

To emphasize the synthetic value of this hydrogenation, the reaction was performed on a gram scale and a TON of 2000, which is the highest TON for this cobalt-catalyzed asymmetric hydrogenation to date, was achieved. Furthermore, the authors performed deuterium labeling experiments and confirmed that H2, and not i-PrOH, is the hydrogen source for the reaction.


 

 


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