Proctor RS. J.
Davis HJ.
Phipps RJ.
* University of Cambridge, UK
Catalytic Enantioselective Minisci-Type Addition to Heteroarenes.
Science 2018;
360: 419-422
Key words
iridium catalysis - photocatalysis - Brønsted acids - Minisci-type reaction - heteroarenes
Significance
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.
Comment
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.
