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Rhodium(<scp>iii</scp>)-catalyzed [5+1] annulation of 2-alkenylphenols with maleimides: access to highly functionalized spirocyclic skeletons

Anil Kumar, Kandikere Ramaiah Prabhu

2021Chemical Communications29 citationsDOI

Abstract

A new edition of [5+1] annulation reaction of maleimides with 2-alkenylphenols has been discovered under a Rh(iii)-catalytic system. The process leads to an efficient synthesis of valued spirocyclic scaffolds bearing an oxygen-containing spiro carbon in a single step and shows a broad substrate scope with good functional group tolerance. The synthetic utility has been exemplified by synthesizing highly functionalized 2,2-disubstituted-2H-chromene skeletons and a gram-scale synthesis with a low catalyst loading.

Topics & Concepts

AnnulationRhodiumCatalysisChemistryCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms
Rhodium(<scp>iii</scp>)-catalyzed [5+1] annulation of 2-alkenylphenols with maleimides: access to highly functionalized spirocyclic skeletons | Litcius