title: Facile Access to Cyclooctanoid Ring Systems via Microwave-Assisted Tandem 6-exo dig Cyclization-Rearrangement Sequence.
abstract: Appropriately substituted 5-alkyn-1-ol systems bearing a nitrile moiety at the triple bond serve as versatile precursors to a variety of cyclooctenone derivatives via a "one-pot" base-catalyzed oxyanionic 6-exo dig cyclization/Claisen rearrangement sequence under microwave irradiation. It was found that the initially formed cyclic intermediate consists of a mixture of endo and exocyclic isomers, which appear to be in equilibrium under the reaction conditions. However, the only observed products from these reactions are α-cyano substituted cyclooctenones, derived from the exocyclic dihydrofuran intermediates.
authors.affiliation: Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, United States of America.
authors.forename: Aaron W
authors.initials: AW
authors.lastname: Feldman
authors.affiliation: Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, United States of America.
authors.forename: Sami I
authors.initials: SI
authors.lastname: Ovaska
authors.affiliation: Department of Chemistry, Connecticut College, 270 Mohegan Avenue, New London, Connecticut 06320, United States of America.
authors.forename: Timo V
authors.initials: TV
authors.lastname: Ovaska