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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

Contributor(s):
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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Further Information

Publication History

Publication Date:
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.


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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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