Hydrogen Atom Transfer-Driven Enantioselective Minisci Reaction of Amides.
Journal of the American Chemical Society
American Chemical Society
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Proctor, R., Chuentragool, P., Colgan, A., & Phipps, R. (2021). Hydrogen Atom Transfer-Driven Enantioselective Minisci Reaction of Amides.. Journal of the American Chemical Society, 143 (13), 4928-4934. https://doi.org/10.1021/jacs.1c01556
Minisci-type reactions constitute one of the most powerful methods for building up complexity around basic heteroarenes. The most desirable variants involve formal oxidative coupling of a C-H bond on each partner, leading back to the simplest pos-sible starting materials. We herein disclose a method which enables such a coupling of linear amides and heteroarenes with full control of enantioselectivity at the newly formed stereocen-ter as well as site-selectivity both on the heteroarene and the amide. This is achieved by use of a chiral phosphoric acid cata-lyst in conjunction with diacetyl as a combined hydrogen atom transfer reagent and oxidant. Diacetyl is directly photoexcitable and thus no extraneous photocatalyst is required, an added fea-ture which contributes to the simplicity and practicality of the protocol.
EPSRC, GlaxoSmithKline, ERC
Royal Society (RGF/EA/180005)
European Commission Horizon 2020 (H2020) ERC (757381)
Embargo Lift Date
External DOI: https://doi.org/10.1021/jacs.1c01556
This record's URL: https://www.repository.cam.ac.uk/handle/1810/319276
Attribution 4.0 International
Licence URL: http://creativecommons.org/licenses/by/4.0/