title: Hydroxyl-directed cyclizations of 1,6-enynes.
abstract: The palladium-catalyzed, hydroxyl-directed cyclization reactions of 1,6-enynes provide a highly diastereoselective process for the syntheses of stereochemically defined cyclopentanes. Consistently high levels of cis-selectivity are possible using homopropargyl alcohols in contrast to the corresponding propargyl alcohols. Hydroborylative enyne cyclizations coupled with this directing group effect provide a useful method for the syntheses of multifaceted compounds bearing all carbon quaternary centers.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station, Austin, Texas 78712, United States.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Camelio
authors.forename: Thomas
authors.initials: T
authors.lastname: Barton
authors.forename: Fenghai
authors.initials: F
authors.lastname: Guo
authors.forename: Travis
authors.initials: T
authors.lastname: Shaw
authors.forename: Dionicio
authors.initials: D
authors.lastname: Siegel
mesh_terms: D002384:Catalysis; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003503:Cyclobutanes; D006574:Heterocyclic Compounds, 2-Ring; D009589:Nitrogen Oxides; C015388:nitrones