Leitch, JA;
de Arriba, ALF;
Tan, J;
Hoff, O;
Martinez, CM;
Dixon, DJ;
(2018)
Photocatalytic reverse polarity Povarov reaction.
Chemical Science
, 9
(32)
pp. 6653-6658.
10.1039/c8sc01704b.
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Abstract
A visible light mediated iridium photocatalysed reverse polarity Povarov reaction of aryl imines and electron deficient alkenes is described. Operating via a putative nucleophilic a-amino radical, generated by a proton coupled electron transfer process, addition to a range of conjugated electron deficient alkene substrates affords substituted tetrahydroquinoline products in high yields and with typically good to excellent diastereoselectivity in favor of the trans diastereoisomer. Sub-stoichiometric quantities of Hantzsch ester were found to be key to initiate the overall redox-neutral, free radical cyclization cascade. This new reaction complements existing two electron Lewis acid mediated variants and expands the capabilities of imine umpolung chemistry to synthetically relevant cyclisation methodology
| Type: | Article |
|---|---|
| Title: | Photocatalytic reverse polarity Povarov reaction |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/c8sc01704b |
| Publisher version: | https://doi.org/10.1039/c8sc01704b |
| 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/10122636 |
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