Vasu, D;
de Arriba, ALF;
Leitch, JA;
de Gombert, A;
Dixon, DJ;
(2019)
Primary alpha-tertiary amine synthesis via alpha-C-H functionalization.
Chemical Science
, 10
(11)
pp. 3401-3407.
10.1039/c8sc05164j.
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Abstract
A quinone-mediated general synthetic platform for the construction of primary a-tertiary amines from abundant primary a-branched amine starting materials is described. This procedure pivots on the efficient in situ generation of reactive ketimine intermediates and subsequent reaction with carboncentered nucleophiles such as organomagnesium and organolithium reagents, and TMSCN, creating quaternary centers. Furthermore, extension to reverse polarity photoredox catalysis enables reactivity with electrophiles, via a nucleophilic a-amino radical intermediate. This efficient, broadly applicable and scalable amine-to-amine synthetic platform was successfully applied to library and API synthesis and in the functionalization of drug molecules.
| Type: | Article |
|---|---|
| Title: | Primary alpha-tertiary amine synthesis via alpha-C-H functionalization |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/c8sc05164j |
| Publisher version: | https://doi.org/10.1039/c8sc05164j |
| Language: | English |
| Additional information: | This article is licensed under a Creative Commons Attribution 3.0 Unported Licence http://creativecommons.org/licenses/by/3.0/ |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10122635 |
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