Synfacts 2018; 14(07): 0705
DOI: 10.1055/s-0037-1610043
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Radical Addition to Heteroarenes

Hisashi Yamamoto
Takahiro Sawano
Proctor RS. J. Davis HJ. Phipps RJ. * University of Cambridge, UK
Catalytic Enantioselective Minisci-Type Addition to Heteroarenes.

Science 2018;
360: 419-422
Further Information

Publication History

Publication Date:
18 June 2018 (online)



Heteroarenes with basic nitrogen centers, such as pyridines or quinolines, can be found in pharmaceuticals and in bioactive molecules. Minisci-type reactions are direct methods to synthesize such classes of compounds, but the generation of highly enantioselective stereocenters is challenging. The authors have developed a highly enantio- and regioselective addition of α-amino alkyl radicals to pyridines and quinolines in the presence of an iridium photoredox catalyst and a chiral Brønsted acid catalyst.



The chiral Brønsted acid activates the heteroarene and induces the enantioselectivity of the reaction, whereas the iridium photoredox catalyst plays a role in the electron-transfer process. In addition to being applicable to a broad scope of substrates, the reaction can be used in late-stage functionalizations of molecules in a highly chemo-, regio-, and enantioselective manner.