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Letter

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

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Jörg T. Binder and Stefan F. Kirsch*

Department Chemie, Technische Universitt Mnchen, Lichtenbergstrasse 4, 85747 Garching, Germany

Org. Lett., 2006, 8 (10), pp 2151–2153

DOI: 10.1021/ol060664z

Publication Date (Web): April 12, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, stefan.kirsch@ch.tum.de

Abstract

In a convenient one-pot process, easily accessed propargyl vinyl ethers and aromatic amines are effectively converted into tetra- and pentasubstituted 5-methylpyrroles which can further be transformed into 5-formylpyrroles via IBX-mediated oxidation. The cascade reaction proceeds through a silver(I)-catalyzed propargyl−Claisen rearrangement, an amine condensation, and a gold(I)-catalyzed 5-exo-dig heterocyclization.

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Published In Issue May 11, 2006
Received March 17, 2006

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Gold(I)-Catalyzed Intramolecular Acetylenic Schmidt Reaction

Palladium-Catalyzed Asymmetric Dearomatization of Naphthalene Derivatives

Platinum- and Gold-Catalyzed Cycloisomerization Reactions of Hydroxylated Enynes

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