Synfacts 2021; 17(06): 0683
DOI: 10.1055/s-0040-1706201
Organo- and Biocatalysis

Enantioselective Minisci-Reaction of N-Heterocycles and Amides through Hydrogen-Atom Transfer

Contributor(s):
Benjamin List
,
Joyce A. A. Grimm
Proctor RS. J, Chuentragool P, Colgan AC, Phipps RJ. * University of Cambridge, UK
Hydrogen Atom Transfer-Driven Enantioselective Minisci Reaction.

J. Am. Chem. Soc. 2021;
143: 4928-4934
DOI: 10.1021/jacs.1c01556.
 

Significance

Phipps and co-workers report a photochemical hydrogen-atom transfer (HAT)-driven enantioselective Minisci reaction of N-heterocycles with amides by using one of a series of chiral phosphoric acids as the chromophore and diacetyl as the terminal oxidant. The corresponding C2-substituted products are obtained in moderate to good yields and with good to excellent enantioselectivities.


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Comment

On the basis of their recent experimental and theoretical investigations (J. Am. Chem. Soc. 2020, 142, 21091), the authors address several limitations, including the laborious synthesis of redox-active esters and low-yielding reactions. The successful introduction of easily accessible N-acylated primary amines as sources of α-amino radicals led to the establishment of a more generally applicable system with a broad substrate scope, with diacetyl as an inexpensive chromophore and chiral phosphoric acids to induce enantioselectivity.


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Publication History

Publication Date:
18 May 2021 (online)

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