title: Enantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis.
abstract: The first catalytic enantioselective Prins cyclization is disclosed. The reaction is catalyzed by the combination of a chiral BINOL-derived bis-phosphoric acid and CuCl. The process consists of a tandem Prins/Friedel-Crafts cyclization that affords the hexahydro-1H-benzo[f]isochromenes products with three new contiguous stereogenic centers in high yields, and good enantio- and excellent diastereoselectivities.
authors.affiliation: Université de Rennes 1, UMR 6226 CNRS, Institut des Sciences Chimiques de Rennes, Equipe PNSCM, UFR des Sciences Biologiques et Pharmaceutiques, 2 Avenue du Prof. Léon Bernard, 35043 Rennes Cedex, France. claudia.lalli@univ-rennes1.fr pierre.van-de-weghe@univ-rennes1.fr.
authors.forename: Claudia
authors.initials: C
authors.lastname: Lalli
authors.forename: Pierre
authors.initials: P
authors.lastname: van de Weghe
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D009284:Naphthols / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry*; D020401:Primed In Situ Labeling / Q000379:methods*; D013237:Stereoisomerism
chemical_list: C406944:BINOL, naphthol; D009284:Naphthols; D010756:Phosphoric Acids; D003300:Copper; C030242:phosphoric acid; C029892:cupric chloride