Tunable Synthesis of 4-Acyl- and 4-Formyl Pyrroles by Rhodium-Catalyzed Ring-Expansion of Azirines with Enaminones.

Org Lett

National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Province Key Laboratory of Natural and Biomimetic Drugs Research, College of Chemistry and Materials, Jiangxi Normal University, Nanchang, Jiangxi 330022, China.

Published: February 2025

A rhodium-catalyzed annulation of 2-azirines with enaminones is presented. This protocol affords a convenient approach to the diversity-oriented synthesis of 4-acyl- and 4-formyl pyrroles with good functional group tolerance. The utility of this reaction has been demonstrated by scale-up preparation, late-stage modification of natural molecules, and synthesis of diverse derivatives.

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http://dx.doi.org/10.1021/acs.orglett.5c00230DOI Listing

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