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Synthesis 2011(12): 2003-2009  
DOI: 10.1055/s-0030-1260466
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones

Mathilde Neel, Jérôme Gouin, Arnaud Voituriez, Angela Marinetti*
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif., 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France
Fax: +33(1)69077247; e-Mail: angela.marinetti@icsn.cnrs-gif.fr;
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Publication History

Received 15 March 2011
Publication Date:
16 May 2011 (online)

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Abstract

Phosphine-promoted [3+2] cyclizations of allenic esters or phosphonates with coumarin derivatives were used to synthesize functionalized bicyclo[4.3.0]chroman-2-ones. Analogous bicy­clo[4.3.0]quinolinones were similarly prepared by a two-step strategy involving a phosphine-catalyzed [3+2] cyclization of diethyl propadienylphosphonate and 3-(2-nitrophenyl)acrylate as the key step. Enantiomerically enriched compounds, with enantiomeric excesses in the range 70-86%, were obtained by using (S,S)-Ferro­PHANE as the chiral catalyst for the cyclization step.

Key words

catalysis - cyclizations - heterocycles - stereoselective synthesis - chromanones

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