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. 2019 Jan 16;141(2):739-742.
doi: 10.1021/jacs.8b09811. Epub 2019 Jan 7.

Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines

Evan P Vanable  1 , Jennifer L Kennemur  1 , Leo A Joyce  2 , Rebecca T Ruck  2 , Danielle M Schultz  2 , Kami L Hull  1
Affiliations

Rhodium-Catalyzed Asymmetric Hydroamination of Allyl Amines

Evan P Vanable et al. J Am Chem Soc. .

Abstract

A Rh-catalyzed enantioselective hydroamination of allylamines using a chiral BIPHEP-type ligand is reported. Enantioenriched 1,2-diamines are formed in good yields and with excellent enantioselectivities. A diverse array of nucleophiles and amine directing groups are demonstrated, including deprotectable motifs. Finally, the methodology was demonstrated toward the rapid synthesis of 2-methyl-moclobemide.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Figure 1
Figure 1
1,2-Diamines in biologically active compounds
Scheme 1
Scheme 1
Hydroamination to afford 1,2-diamines
See this image and copyright information in PMC

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