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Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL
Yong Guan1, Zhensheng Ding, William D Wulff
1Department of Chemistry, Michigan State University, East Lansing, MI 48824 (USA).
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.
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