New synthesis of vaulted biaryl ligands via the Snieckus phenol synthesis.
[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.
Yu
Su
S
Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
Rabalakos
Constantinos
C
Mitchell
William D
WD
Wulff
William D
WD
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*
D000577:Amides; D007202:Indicators and Reagents; D008024:Ligands; D009281:Naphthalenes; D010616:Phenanthrenes; D010636:Phenols; D011084:Polycyclic Aromatic Hydrocarbons; C510253:VAPOL ligand; D002857:Chromium