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Synfacts 2021; 17(07): 0767
DOI: 10.1055/s-0040-1720440
Metals in Synthesis

Ruthenium-Catalyzed Enantioselective Reductive Amination

Contributor(s):
Paul Knochel
,
Johannes H. Harenberg
Yamada M, *, Azuma K, Yamano M. Takeda Pharmaceutical Company Limited, Osaka, Japan
Highly Enantioselective Direct Asymmetric Reductive Amination of 2‑Acetyl-6-Substituted Pyridines.

Org. Lett. 2021;
23: 3364-3367
DOI: 10.1021/acs.orglett.1c00848.
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Key words

ruthenium catalysis - reductive amination - asymmetric synthesis

Significance

The authors report a ruthenium-catalyzed reductive amination of ketones. Ru-(OAc)2((S)-binap) is used as catalyst and ammonium trifluoroacetate as the nitrogen source; hydrogen pressures of 0.8 MPa are needed. The procedure allows the formation of chiral amines in high enantiomeric excess and quantitative conversions. Sensitive functional groups such as esters and ­amides are tolerated.


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Comment

Reductive aminations are widespread reactions in the pharmaceutical industry. This ­direct asymmetric reductive amination allows for the generation of chiral secondary amines from ­ketones, which has been challenging before. Diarylketones, fused ring ketones, and 2-acetyl-6-pyridone showed no reaction under these conditions


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Publication History

Article published online:
17 June 2021

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