Photocatalytic reverse polarity Povarov reaction

11Citations
Citations of this article
23Readers
Mendeley users who have this article in their library.

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 α-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.

Cite

CITATION STYLE

APA

Leitch, J. A., Fuentes De Arriba, A. L., Tan, J., Hoff, O., Martínez, C. M., & Dixon, D. J. (2018). Photocatalytic reverse polarity Povarov reaction. Chemical Science, 9(32), 6653–6658. https://doi.org/10.1039/c8sc01704b

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free