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Synthesis of Highly Substituted Pyrroles via a Multimetal-Catalyzed Rearrangement-Condensation-Cyclization Domino Approach

Jörg T. Binder and Stefan F. Kirsch*

*Department Chemie, Technische Universität München, Lichtenbergstrasse 4, 85747 Garching, Germany, Email: stefan.kirschch.tum.de

J. T. Binder, S. F. Kirsch, Org. Lett., 2006, 8, 2151-2153.

DOI: 10.1021/ol060664z (free Supporting Information)


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Abstract

Propargyl vinyl ethers and aromatic amines are effectively converted into tetra- and pentasubstituted 5-methylpyrroles through a silver(I)-catalyzed propargyl-Claisen rearrangement, an amine condensation, and a gold(I)-catalyzed 5-exo-dig heterocyclization in a convenient one-pot process.

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Gold(I)-Catalyzed Synthesis of Highly Substituted Furans

M. H. Suhre, M. Reif, S. F. Kirsch, Org. Lett., 2005, 7, 3873-3876.


Key Words

Pyrroles, Claisen rearrangement


ID: J54-Y2006-1340