Concepedia

Expedient Synthesis of Highly Substituted Pyrroles via Tandem Rearrangement of α-Diazo Oxime Ethers

Yaojia Jiang, Wei Chuen Chan, Cheol‐Min Park

Journal of the American Chemical Society · 2012 · 168 citations · 44 references

DOI

Concepts

Abstract

An efficient rhodium-catalyzed synthesis of 2H-azirines and pyrroles has been developed. Novel rearrangement of α-oximino ketenes derived from α-diazo oxime ethers provides 2H-azirines bearing quaternary centers and allows for subsequent rearrangement to highly substituted pyrroles in excellent yields.

References

44

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100 Years of the Wolff Rearrangement

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Total Syntheses of Ningalin A, Lamellarin O, Lukianol A, and Permethyl Storniamide A Utilizing Heterocyclic Azadiene Diels−Alder Reactions

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The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3‐Aliphatic‐Substituted Indoles and Pyrroles

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Pyrrole Syntheses by Multicomponent Coupling Reactions

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