Catalytic enantioselective Minisci-type addition to heteroarenes
Year: 2018
Type: article
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.
Source: Science
Institution: University of Cambridge
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Estimated APC paid: $1,208
Awards: RS Fellow - EPSRC grant (2014): Application of Tandem Non-Covalent Interactions to the Development of New Enantioselective Reactions, Developing a Catalytic Strategy to Address Regiocontrol in Radical Reactions of Aromatic Heterocycles, Developing a Catalytic Strategy to Address Regiocontrol in Radical Reactions of Aromatic Heterocycles, G8988900908
OpenAlex ID: W2795687764