Visible‐Light‐Induced Oxidation/[3+2] Cycloaddition/Oxidative Aromatization Sequence: A Photocatalytic Strategy To Construct Pyrrolo[2,1‐<i>a</i>]isoquinolines

You‐Quan Zou(Central China Normal University), Liang‐Qiu Lu(Central China Normal University), Liang Fu(Central China Normal University), Ning‐Jie Chang(Central China Normal University), Jian Rong(Central China Normal University), Jia‐Rong Chen(Central China Normal University), Wen‐Jing Xiao(Central China Normal University)
Angewandte Chemie International Edition
June 22, 2011
Cited by 432

Abstract

A ray of sunshine: The title reaction sequence using ethyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with a series of electron-deficient alkenes and alkynes provides rapid and efficient access to pyrrolo[2,1-a]isoquinolines (see scheme; bpy=2,2′-bipyridine, EWG=electron-withdrawing group). The reaction offers a strategically new protocol for the direct and efficient construction of the core structure of naturally occurring lamellarin alkaloids.


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