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

Key words

Minisci reaction - hydrogen-atom transfer - aza-heterocycles - phosphoric acids

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.

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.

Publication History

Article published online:
18 May 2021