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Photocatalytic reverse polarity Povarov reaction

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. Green open access

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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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