title: New synthesis of vaulted biaryl ligands via the Snieckus phenol synthesis.
abstract: [reaction: see text] In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route was examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus. The latter derivatives could be converted in a two-step sequence to 2-phenyl-4-phenanthrols in 60-72% overall yields. The utility of this method for the synthesis of VAPOL derivatives is demonstrated in the synthesis of (S)-7,7'-dimethyl-VAPOL.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors.forename: Su
authors.initials: S
authors.lastname: Yu
authors.forename: Constantinos
authors.initials: C
authors.lastname: Rabalakos
authors.forename: William D
authors.initials: WD
authors.lastname: Mitchell
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D055598:Chemical Phenomena; D002621:Chemistry; D002857:Chromium; D003500:Cyclization; D007202:Indicators and Reagents; D008024:Ligands; D009281:Naphthalenes / Q000737:chemistry; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000138:chemical synthesis*; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*
chemical_list: D000577:Amides; D007202:Indicators and Reagents; D008024:Ligands; D009281:Naphthalenes; D010616:Phenanthrenes; D010636:Phenols; D011084:Polycyclic Aromatic Hydrocarbons; C510253:VAPOL ligand; D002857:Chromium