Synfacts 2018; 14(06): 0639
DOI: 10.1055/s-0037-1609986
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Cation Radical Diels–Alder Reactions via Asymmetric Counteranion-Directed Catalysis

Benjamin List
Nobuya Tsuji
Morse PD. Nguyen TM. Cruz CL. Nicewicz DA. * The University of North Carolina at Chapel Hill, USA
Enantioselective Counter-Anions in Photoredox Catalysis: The Asymmetric Cation Radical Diels–Alder Reaction.

Tetrahedron 2018;
DOI: 10.1016/j.tet.2018.03.052.
Further Information

Publication History

Publication Date:
17 May 2018 (online)



The Nicewicz group reports both intra- and intermolecular enantioselective Diels–Alder reactions. The photoredox catalyst system consists of a cationic oxopyrylium photooxidant bearing a chiral N-triflyl phosphoramide anion.



Enantioselective transformations that proceed through a radical ion pair represent a major challenge for asymmetric catalysis. In this report, despite obtaining moderate enantioselectivities, the authors proved the concept by introducing a chiral counteranion. The presented results could provide insights into asymmetric photoredox reactions.