title: Diastereoselective Friedel-Crafts alkylation of hydronaphthalenes.
abstract: An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intramolecular Friedel-Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.
authors.affiliation: Davenport Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S3H6, Canada.
authors.forename: Jennifer
authors.initials: J
authors.lastname: Tsoung
authors.forename: Katja
authors.initials: K
authors.lastname: Krämer
authors.forename: Adam
authors.initials: A
authors.lastname: Zajdlik
authors.forename: Clemence
authors.initials: C
authors.lastname: Liébert
authors.forename: Mark
authors.initials: M
authors.lastname: Lautens
mesh_terms: D000478:Alkylation; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D013764:Tetrahydronaphthalenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009281:Naphthalenes; D013764:Tetrahydronaphthalenes