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Synfacts 2020; 16(08): 0959
DOI: 10.1055/s-0040-01707439
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Enzyme-Catalyzed Asymmetric Primary Amination of Benzylic and Allylic C(sp3)–H Bonds

Contributor(s):
Benjamin List
,
Oleg Grossmann
Jia Z.-J, Gao S, Arnold FH. * California Institute of Technology, Pasadena, USA
Enzymatic Primary Amination of Benzylic and Allylic C(sp3)–H Bonds.

J. Am. Chem. Soc. 2020;
142: 10279-10283
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Further Information

Publication History

Publication Date:
21 July 2020 (online)

 
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Key words

amines - directed evolution - cytochrome P411 hydroxylamines - amination - C–H bond activation

Significance

The Arnold group reports the directed evolution of P411-B2 to give efficient benzylic (P411BPA) and allylic (P411APA) C–H aminases. By using hydroxylamine derivatives as nitrogen sources under anaerobic conditions, the authors converted a variety of benzylic and allylic C(sp3)–H bonds into primary amines in good yields with high chemo- and enantioselectivities and promising regioselectivities­.


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Comment

This work represents a milestone in the development of a general C–H amination reaction. Mechanistic investigations are highly desirable in further developing this method to overcome the limitation toward alkyl-substituted allyl systems. In addition, this work encourages and challenges other groups to develop small-molecule catalysts to enable this reaction.


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