title: Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.
abstract: The active site in the BOROX catalyst is a chiral polyborate anion (boroxinate) that is assembled in situ from three equivalents of B(OPh)3 and one of the VANOL ligand by a molecule of substrate. The substrates are bound to the boroxinate by H bonds to oxygen atoms O1-O3. The effects of introducing substituents at each position of the naphthalene core of the VANOL ligand are systematically investigated in an aziridination reaction. Substituents in the 4,4'- and 8,8'-positions have a negative effect on catalyst performance, whereas, substituents in the 7- and 7'-positions have the biggest impact in a positive direction.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI 48824 (USA).
authors.forename: Yong
authors.initials: Y
authors.lastname: Guan
authors.forename: Zhensheng
authors.initials: Z
authors.lastname: Ding
authors.forename: William D
authors.initials: WD
authors.lastname: Wulff
mesh_terms: D000838:Anions / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000838:Anions; D001388:Aziridines; D001881:Borates; D009281:Naphthalenes; C530040:VANOL ligand
keywords: asymmetric catalysis; biaryls; catalysis; structure-activity relationships