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

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.


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.



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.


Publication History

Publication Date:
18 May 2021 (online)

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