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Synlett 2011(9): 1259-1261  
DOI: 10.1055/s-0030-1260542
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© Georg Thieme Verlag Stuttgart ˙ New York

Intramolecular Nitroalkene Diels-Alder Reaction Catalyzed by Brønsted Acids

Andreina Aguado, Norito Takenaka*
Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146-0431, USA
Fax: +1(305)2844571; e-Mail: n.takenaka@miami.edu;
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Publication History

Received 31 January 2011
Publication Date:
20 April 2011 (online)

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Abstract

Brønsted acid catalysis of intramolecular Diels-Alder cyclizations of (E)-1-nitro-1,6,8-nonatrienes and (E)-1-nitro-1,7,9-decatrienes was investigated. Catalyzed reactions showed significantly higher endo selectivities than the corresponding thermal reactions. To our knowledge, this is the first example of catalysis (substoichiometric amount of catalysts) of the intramolecular nitroalkene Diels-Alder reaction.

Key words

Brønsted acid catalysis - intramolecular Diels-Alder cyclizations - catalysis

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9

NaBArF24˙(H2O)x(PhOH)y was obtained by refluxing a mixture of NaBArF24˙2.5H2O and PhOH (2.5 equiv) in toluene, followed by removal of toluene.

17

Knochel and co-workers reported that silica gel promoted the cyclization of (1E,6E,8E)-1-nitro-1,6,8-nonatriene in hexane. See ref. 2e.