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Catalytic enantioselective Minisci-type addition to heteroarenes.

Accepted version
Peer-reviewed

Type

Article

Change log

Abstract

Basic heteroarenes are a ubiquitous feature of pharmaceuticals and bioactive molecules, and Minisci-type additions of radical nucleophiles are a leading method for their elaboration. Despite many Minisci-type protocols that result in the formation of stereocenters, exerting control over the absolute stereochemistry at these centers remains an unmet challenge. We report a process for addition of prochiral radicals, generated from amino acid derivatives, to pyridines and quinolines. Our method offers excellent control of both enantioselectivity and regioselectivity. An enantiopure chiral Brønsted acid catalyst serves both to activate the substrate and induce asymmetry, while an iridium photocatalyst mediates the required electron transfer processes. We anticipate that this method will expedite access to enantioenriched small-molecule building blocks bearing versatile basic heterocycles.

Description

Keywords

0306 Physical Chemistry (incl. Structural)

Journal Title

Science

Conference Name

Journal ISSN

0036-8075
1095-9203

Volume Title

360

Publisher

American Association for the Advancement of Science (AAAS)
Sponsorship
Engineering and Physical Sciences Research Council (EP/N005422/1)
The Royal Society (uf130004)
Engineering and Physical Sciences Research Council (1918560)
EPSRC (1800778)