Hydrogen Atom Transfer-Driven Enantioselective Minisci Reaction of Amides.
J Am Chem Soc
American Chemical Society (ACS)
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Proctor, R. S., Chuentragool, P., Colgan, A. C., & Phipps, R. J. (2021). Hydrogen Atom Transfer-Driven Enantioselective Minisci Reaction of Amides.. J Am Chem Soc, 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 possible starting materials. We herein disclose a method that enables such a coupling of linear amides and heteroarenes with full control of enantioselectivity at the newly formed stereocenter as well as site selectivity on both the heteroarene and the amide. This is achieved by the use of a chiral phosphoric acid catalyst 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 feature that contributes to the simplicity and practicality of the protocol.
EPSRC, GlaxoSmithKline, ERC
Royal Society (RGF/EA/180005)
European Research Council (757381)
Engineering and Physical Sciences Research Council (EP/S03269X/1)
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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/