title: Planar Chiral Phosphoramidites with a Paracyclophane Scaffold: Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes.
abstract: The key structural feature of the new phosphoramidites is a paracyclophane scaffold in which two aryl rings are tethered by both a 1,8-biphenylene unit and a O-P-O bridge. Suitable aryl substituents generate planar chirality. The corresponding gold(I) complexes promote the cycloisomerization of prochiral nitrogen-tethered dienynes. These reactions afford bicyclo[4.1.0]heptene derivatives displaying three contiguous stereogenic centers, with very high diastereoselectivity and up to 95 % ee.
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Wu
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France.
authors.forename: Kévin
authors.initials: K
authors.lastname: Isaac
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France. arnaud.voituriez@cnrs.fr.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Betzer
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France. jean-francois.betzer@cnrs.fr.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Voituriez
authors.affiliation: Institut de Chimie des Substances Naturelles, ICSN - CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198, Gif-sur-Yvette, France.
authors.forename: Angela
authors.initials: A
authors.lastname: Marinetti
keywords: cycloisomerization; enantioselectivity; gold catalysis; phosphoramidite; planar chirality