An unexpectedly mild thermal alder-ene-type cyclization of enallenes
Stockholm University, Faculty of Science, Department of Organic Chemistry2006 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, ISSN 0022-3263, Vol. 71, no 7, 2914-2917 p.Article in journal (Refereed) Published
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 degrees 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.
Place, publisher, year, edition, pages
American Chemical Society (ACS), 2006. Vol. 71, no 7, 2914-2917 p.
pd-catalyzed cycloisomerization, allenes, 1, 2-dialkylidenecycloalkanes, carbocyclization, alkylallene, alkenes
IdentifiersURN: urn:nbn:se:su:diva-25281DOI: 10.1021/jo060013gOAI: oai:DiVA.org:su-25281DiVA: diva2:199320
Part of urn:nbn:se:su:diva-7942006-01-122006-01-122013-08-14Bibliographically approved