An Unexpectedly Mild Thermal Alder−Ene-Type Cyclization of Enallenes

A mild, thermal Alder−ene reaction of enallenes has been developed. The allenic double bond acts as the “ene” and generates a carbon−carbon bond to an unactivated olefinic “enophile” in DMF at 120 °C to give [n.3.0] bicyclic systems (n = 3−5) in good yields. Except for a minor [2 + 2] cycloaddition...

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Veröffentlicht in:Journal of organic chemistry 2006-03, Vol.71 (7), p.2914-2917
Hauptverfasser: Närhi, Katja, Franzén, Johan, Bäckvall, Jan-E
Format: Artikel
Sprache:eng
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Zusammenfassung:A mild, thermal Alder−ene reaction of enallenes has been developed. The allenic double bond acts as the “ene” and generates a carbon−carbon bond to an unactivated olefinic “enophile” in DMF at 120 °C to give [n.3.0] bicyclic systems (n = 3−5) in good yields. Except for a minor [2 + 2] cycloaddition byproduct, the reaction proceeded with complete atom economy, as there is no requirement of a catalyst or additional reactants, and no waste products are formed in the process.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo060013g