Rhodium-Catalyzed Asymmetric Arylative Ring-Opening Reactions of Heterobicyclic Alkenes with Anilines

Organic Letters
Jingchao ChenBaomin Fan

Abstract

Asymmetric arylative ring-opening reactions of heterobicyclic alkenes with anilines have been reported for the first time. A wide range of heterobicyclic alkenes, including azabenzonorbornadienes and oxabenzonorbornadienes, were well tolerated in the reaction with various anilines, and they generally delivered the corresponding chiral aryltetralin derivatives in good to excellent enantioselectivities. The reaction is speculated to proceed through the Friedel-Crafts reaction pathway.

References

Apr 12, 2003·Organic Letters·Ramón Gómez ArrayásJuan C Carretero
Jan 6, 2004·Angewandte Chemie·Séverine JeulinPhilippe Dellis
Jan 27, 2004·Angewandte Chemie·Marco BandiniAchille Umani-Ronchi
Feb 8, 2007·Journal of the American Chemical Society·Takahiro NishimuraTamio Hayashi
May 27, 2008·Chemical Reviews·Thomas B Poulsen, Karl Anker Jørgensen
Jul 23, 2009·Chemical Society Reviews·Shu-Li YouMi Zeng
Nov 28, 2013·The Journal of Organic Chemistry·Xuejing PanDingqiao Yang
Jun 30, 2015·Journal of the American Chemical Society·Bin XuQi-Lin Zhou
Jun 2, 2017·Angewandte Chemie·José Tiago Menezes CorreiaFernando Coelho

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