Inter-and Intramolecular [4 + 2] Cycloadditions of Nitroalkenes with Olefins. 2-Nitrostyrenes

Scott E. Denmark, Brenda S. Kesler, Young Choon Moon

Research output: Contribution to journalArticlepeer-review


Aromatic nitroalkenes 9-12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitironates 25-30 with exclusive anti selectivity. Hammett studies helped to further delineate the role of the Lewis acid. Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions. The major products were the syn diastereomers which arise from an endo-folded transition structure. Finally, intramolecular cycloaddition of 36-39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.

Original languageEnglish (US)
Pages (from-to)4912-4924
Number of pages13
JournalJournal of Organic Chemistry
Issue number18
StatePublished - Aug 1 1992

ASJC Scopus subject areas

  • Organic Chemistry


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