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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.

SUBMITTER: Guan Y 

PROVIDER: S-EPMC3947456 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Vaulted biaryls in catalysis: A structure-activity relationship guided tour of the immanent domain of the VANOL ligand.

Guan Yong Y   Ding Zhensheng Z   Wulff William D WD  

Chemistry (Weinheim an der Bergstrasse, Germany) 20131002 46

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 eff  ...[more]

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