The Role of N-Substitution in Regio- and Stereoselective Vinylogous Imidonaphthoquinone (VINAquinone) [2 + 2] Photocycloadditions
Ian Merski,
Jinya Yin,
Ryan T. VanderLinden
et al.
Abstract:Described in this manuscript are intramolecular [2 + 2] photocycloadditions of readily available vinylogous imidonaphthoquinones whose regio-and diastereoselectivity is dependent on the substitution on the vinylogous imide. When exposed to 419 nm light, 2°vinylogous imidonaphthoquinones give novel bridged tetracyclic aza-anthraquinones from a rare crossed [2 + 2] cycloaddition reaction. In contrast, exposure of the corresponding 3°substrates to white light leads to linear adducts. Also outlined here are auxili… Show more
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