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Issue 53, 2016
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Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides

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Abstract

Atropisomeric maleimides were synthesized and subjected to atropselective [5+2]-photocycloaddition under direct irradiation to yield azepinone products with high enantio- (ee >98%) and diastereoselectivity (dr >98%). While the ee was dictated by the axial chirality, the dr was influenced by the substituent on the maleimide ring. Interestingly, by tuning the electronics of the substituent, the dr of the product can be reversed.

Graphical abstract: Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides

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Article information


Submitted
08 Apr 2016
Accepted
21 May 2016
First published
14 Jun 2016

Chem. Commun., 2016,52, 8305-8308
Article type
Communication

Engaging electronic effects for atropselective [5+2]-photocycloaddition of maleimides

R. Raghunathan, E. Kumarasamy, S. Jockusch, A. Ugrinov and J. Sivaguru, Chem. Commun., 2016, 52, 8305
DOI: 10.1039/C6CC02962K

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