Intramolecular Diels-Alder reaction of 1-nitrodeca-1,6,8-trienes

Mark J. Kurth, Michael J. O'Brien, Håkon Hope, Michael Yanuck

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Nitro trienes 1, 2, and 3 are prepared from nona-5,7-dien-1-ols 6, 10, and 14, respectively, via a three-step sequence involving PCC oxidation, nitro aldol condensation, and dehydration. Intramolecular Diels-Alder reaction of nitro trienes 1 and 2 preferentially affords endo cycloadducts possessing the trans ring fusion (9:1 trans/cis) while cyclization of 3 gives exclusively the trans-fused perhydroindene skeleton (25c/25d, 9:1). In contrast, (Z)-nitroolefins 4 and 5, which are found to undergo cyclization at room temperature, produce a nearly 1:1 mixture of cis- and trans-fused cycloadducts.

Original languageEnglish (US)
Pages (from-to)2626-2632
Number of pages7
JournalJournal of Organic Chemistry
Issue number15
StatePublished - 1985


ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kurth, M. J., O'Brien, M. J., Hope, H., & Yanuck, M. (1985). Intramolecular Diels-Alder reaction of 1-nitrodeca-1,6,8-trienes. Journal of Organic Chemistry, 50(15), 2626-2632.