Intramolecular Nitroalkene Diels-Alder Reaction Catalyzed by Brønsted Acids

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

References and Notes

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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.