title: Doubly Vinylogous Aldol Reaction of Furoate Esters with Aldehydes and Ketones.
abstract: The use of bulky Lewis acids, aluminum tris(2,6-diphenylphenoxide) (ATPH) and aluminum tris(2,6-di-2-naphthylphenoxide) (ATNP), in the doubly vinylogous aldol reaction between methyl-5-methyl-2-furoate and aldehydes or ketones is described. These reactions proceed smoothly and in high yields with both enolizable and non-enolizable substrates. This C-C bond-forming reaction enables a new bond construction for the synthesis of functionalized furans.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309-0215, United States.
authors.forename: William T
authors.initials: WT
authors.lastname: Hartwig
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80309-0215, United States.
authors.forename: Tarek
authors.identifier: 0000-0003-3703-5672
authors.initials: T
authors.lastname: Sammakia
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000447:Aldehydes; D004952:Esters; D005663:Furans; D007659:Ketones; D014753:Vinyl Compounds