Issue 13, 2024

Light-mediated catalytic enantioselective difluoroalkylation of β-ketoesters via phase-transfer catalysis

Abstract

We report a phase-transfer-catalysed asymmetric α-difluoroalkylation of β-ketoesters through visible light-promoted radical generation. This methodology affords quaternary stereocentres with mild enantioenrichment and isolated yields up to 99%. Through mechanistic investigations, we have determined that the reaction proceeds via difluoroalkyl radical generation arising from an in situ electron donor–acceptor complex capable of absorbing visible light. Extensive optimisation of the reaction parameters was carried in an attempt to overcome a facile racemic background reaction.

Graphical abstract: Light-mediated catalytic enantioselective difluoroalkylation of β-ketoesters via phase-transfer catalysis

Supplementary files

Article information

Article type
Research Article
Submitted
29 Feb 2024
Accepted
09 May 2024
First published
09 May 2024
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2024,11, 3639-3647

Light-mediated catalytic enantioselective difluoroalkylation of β-ketoesters via phase-transfer catalysis

C. E. Adams and C. P. Johnston, Org. Chem. Front., 2024, 11, 3639 DOI: 10.1039/D4QO00390J

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