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Synthesis 2010(1): 161-170  
DOI: 10.1055/s-0029-1217046
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Diels-Alder Reactions of Vinylindoles Using Organocatalysis

Claudio Gioia, Luca Bernardi*, Alfredo Ricci*
Department of Organic Chemistry ‘A. Mangini’, University of Bologna, viale Risorgimento 4, 40136 Bologna, Italy
Fax: +39(051)2093654; e-Mail: nacca@ms.fci.unibo.it; e-Mail: ricci@ms.fci.unibo.it;
Further Information

Publication History

Received 28 July 2009
Publication Date:
19 October 2009 (online)

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Abstract

The different behavior of 3- and 2-vinylindoles in Diels-Alder cycloaddition reactions in the presence of bifunctional hydrogen bond donor organocatalysts is described.

Key words

asymmetric catalysis - Diels-Alder reactions - kinetic resolution - organocatalysis - vinylindoles

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32

Obtained from (R)-bornylamine and 1,1′-thiocarbonyl-diimidazole in THF, followed by chromatographic purification.