Highly selective palladium-catalyzed synthesis of protected alpha,beta-unsaturated methyl ketones and 2-alkoxy-1,3-butadienes. High-speed chemistry by microwave flash heating
2000 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 65, no 15, 4537-4542 p.Article in journal (Refereed) PublishedText
A selective and mild procedure is described for the direct synthesis of 2-alkene-2-methyl-1,3-dioxolanes via regiocontrolled Heck vinylation of commercially available 2-hydroxyethyl vinyl ether. The procedure permits chemoselective transformation of a vinylic triflate or bromide into a blocked alpha,beta-unsaturated methyl ketone. Furthermore, a significantly improved and highly regioselective synthesis of 2-alkoxy-1,3-butadienes has been developed. Flash heating by microwave irradiation promotes the palladium-catalyzed reactions, and the starting materials are fully converted after reaction times of 5-7 min.
Place, publisher, year, edition, pages
Uppsala Univ, Uppsala Biomed Ctr, Dept Organ Pharmaceut Chem, SE-75123 Uppsala, Sweden., 2000. Vol. 65, no 15, 4537-4542 p.
IdentifiersURN: urn:nbn:se:uu:diva-275428DOI: 10.1021/jo000070oISI: 000088488900010OAI: oai:DiVA.org:uu-275428DiVA: diva2:900261