title: Development of Enantioselective Palladium-Catalyzed Alkene Carboalkoxylation Reactions for the Synthesis of Tetrahydrofurans.
abstract: The Pd-catalyzed coupling of γ-hydroxyalkenes with aryl bromides affords enantiomerically enriched 2-(arylmethyl)tetrahydrofuran derivatives in good yield and up to 96:4 e.r. This transformation was achieved through the development of a new TADDOL/2-arylcyclohexanol-derived chiral phosphite ligand. The transformations are effective with an array of different aryl bromides, and can be used for the preparation of products bearing quaternary stereocenters.
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA).
authors.forename: Brett A
authors.initials: BA
authors.lastname: Hopkins
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA).
authors.forename: Zachary J
authors.initials: ZJ
authors.lastname: Garlets
authors.affiliation: Department of Chemistry, University of Michigan, 930. N. University Ave, Ann Arbor, MI 48109-1055 (USA). jpwolfe@umich.edu.
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D005663:Furans; D009942:Organometallic Compounds; D010165:Palladium
keywords: asymmetric catalysis; enantioselective synthesis; heterocycles; palladium