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Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones

Supporting Info

Julie Moreau†, Claudie Hubert†, Jessika Batany†, Loic Toupet‡, Thierry Roisnel§, Jean-Pierre Hurvois† and Jean-Luc Renaud*

^† Sciences Chimiques de Rennes, Catalyse et Organom

talliques, UMR 6226

^‡ Institut de Physique de Rennes, Groupe Mati

re Condens

e et Mat

riaux, UMR 6626

^§ Sciences Chimiques de Rennes, Diffraction Rayons-X, UMR 6226

CNRS-Universit

de Rennes 1, Campus de Beaulieu-35042 Rennes Cedex, France

Laboratoire de Chimie Mol

culaire et Thioorganique, UMR 6507, INC3M, FR 3038, ENSICAEN-Universit

de Caen, 14050 Caen, France

J. Org. Chem., 2009, 74 (23), pp 8963–8973

DOI: 10.1021/jo901238y

Publication Date (Web): November 12, 2009

, *To whom correspondence should be addressed. Fax: 33(0)231452877. Phone: 33(0)231452842.

Abstract

Brønsted acids catalyze the addition of enolizable β-diketones, β-ketoesters, and vinylogous amides to α,β-unsaturated aldehydes to lead to substituted chromenones, pyranones, and tetrahydroquinolinones in good yields under mild reaction conditions via a formal [3 + 3] cycloaddition.

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Published In Issue December 04, 2009
Article ASAPNovember 12, 2009
Received: June 17, 2009

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Article

Metal-Free Brønsted Acid Catalyzed Formal [3 + 3] Annulation. Straightforward Synthesis of Dihydro-2H-Chromenones, Pyranones, and Tetrahydroquinolinones

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Related Content

Enantioselective Total Synthesis of (−)-Acutumine

Lewis Acid Catalyzed Indole Synthesis via Intramolecular Nucleophilic Attack of Phenyldiazoacetates to Iminium Ions

Expanding the Scope of Cinchona Alkaloid-Catalyzed Enantioselective α-Aminations of Oxindoles: A Versatile Approach to Optically Active 3-Amino-2-oxindole Derivatives

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