Dual C-H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels-Alder reaction

Described herein is the first example of the application of an iminium intermediate generated by visible-light photocatalyzed oxidation in an inverse electron-demand aza-Diels-Alder reaction. This dual functionalization of both C(sp(3))-H and C(sp(2))-H bonds of N-aryl tetrahydroisoquinolines repres...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (6), p.1190-1193
Main Authors: Xu, Guo-Qiang, Li, Chen-Guang, Liu, Ming-Qian, Cao, Jian, Luo, Yong-Chun, Xu, Peng-Fei
Format: Article
Language:English
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Summary:Described herein is the first example of the application of an iminium intermediate generated by visible-light photocatalyzed oxidation in an inverse electron-demand aza-Diels-Alder reaction. This dual functionalization of both C(sp(3))-H and C(sp(2))-H bonds of N-aryl tetrahydroisoquinolines represents a valuable example for access to polycycles with high diastereoselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08833j