Synfacts 2018; 14(07): 0753
DOI: 10.1055/s-0037-1610083
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Cooperative Catalysis: Radical Addition to Olefins and Asymmetric Protonation

Benjamin List
David Díaz-Oviedo
Yin Y. Dai Y. Jia H. Li J. Bu L. Qiao B. Zhao X. Jiang Z. * Henan University and Henan University of Technology, P. R. of China
Conjugate Addition–Enantioselective Protonation of N-Aryl Glycines to α-Branched 2-Vinylazaarenes via Cooperative Photoredox and Asymmetric Catalysis.

J. Am. Chem. Soc. 2018;
140: 6083-6087
Further Information

Publication History

Publication Date:
18 June 2018 (online)



Jiang and co-workers report the enantioselective radical conjugate addition–­protonation of N-aryl glycines to α-branched vinyl­azaarenes using a metal-free dual catalytic system (a photosensitizer and a chiral phosphoric acid). The corresponding products are obtained in high yields with good to excellent enantioselectivities, and the methodology is applied to the synthesis of the medicinal compound pheniramine.



Because α-amino acids are abundant, their use as starting materials for organic synthesis is desirable. In this report, N-aryl α-glycines undergo photooxidative decarboxylation and react further with highly activated olefins in a radical pathway followed by enantioselective protonation. While many examples are shown, the presented substrate scope is still limited to pyridine- and quinoline-containing substances.