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Synthesis of Cyclopropanes via 1,3-Migration of Acyloxy Groups Triggered by Formation of α-Imino Rhodium Carbenes

Ze‐Feng Xu, Jincheng Liu, Xin Chang, Tao Chen, Huaping Xu, Shengguo Duan, Chuan‐Ying Li

2020Organic Letters34 citationsDOI

Abstract

A novel and highly efficient synthetic approach to cyclopropanes was realized via 1,3-migration of acyloxy groups triggered by α-imino rhodium carbenes. Excellent chemoselectivity ensured broad compatibility of common functional groups. Merits such as readily available substrates, mild reaction conditions, and time-saving processes qualified this transformation as an attractive alternative strategy to synthesize multifunctionalized cyclopropanes. Primary investigations and discussion on the mechanism are presented.

Topics & Concepts

ChemistryRhodiumChemoselectivityCombinatorial chemistryCatalysisCompatibility (geochemistry)StereochemistryOrganic chemistryChemical engineeringEngineeringCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods
Synthesis of Cyclopropanes via 1,3-Migration of Acyloxy Groups Triggered by Formation of α-Imino Rhodium Carbenes | Litcius