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Rh(III)-Catalyzed [4 + 2] Annulation of 3-Aryl-5-isoxazolone with Maleimides or Maleic Ester

Ting Wan, Chao Pi, Yangjie Wu, Xiuling Cui

2020Organic Letters40 citationsDOI

Abstract

The Rh(III)-catalyzed [4 + 2] annulation of 3-aryl-5-isoxazolones with maleimides or maleic ester has been developed, which gives synthetically important 3,4-dihydroisoquinoline derivatives in good to excellent yields. This facile protocol can tolerate a variety of functional groups, and CO2 was produced as the predominant byproduct. Notably, a C–C bond and a C–N bond were formed simultaneously. This protocol could be easily scaled up.

Topics & Concepts

ChemistryAnnulationArylCatalysisMedicinal chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms
Rh(III)-Catalyzed [4 + 2] Annulation of 3-Aryl-5-isoxazolone with Maleimides or Maleic Ester | Litcius