Osminski, Wynter E. G.; Lu, Zhenjie; Zhao, Wenjun; Mohammadlou, Aliakbar; Yin, Xiaopeng; Matthews, Emily C.; Canestraight, Virginia M.; Staples, Richard J.; Allen, Connor J.; Hirschi, Jennifer S.; Wulff, William D. published the artcile< Probing Catalyst Function - Electronic Modulation of Chiral Polyborate Anionic Catalysts>, SDS of cas: 623-50-7 , the main research area is aziridine synthesis aziridiation electronic modulation chiral polyborate catalyst.
Boroxinate complexes of VAPOL and VANOL are a chiral anionic platform that can serve as a versatile staging arena for asym. catalysis. The structural underpinning of the platform is a chiral polyborate core that covalently links together alcs. (or phenols) and vaulted biaryl ligands. The polyborate platform is assembled in situ by the substrate of the reaction, and thus a multiplex of chiral catalysts can be rapidly assembled from various alcs. (or phenols) and bis-phenol ligands for screening of catalyst activity. In the present study, variations in the steric and electronic properties of the phenol/alc. component of the boroxinate catalyst are probed to reveal their effects on the asym. induction in the catalytic asym. aziridination reaction. A Hammett study is consistent with a mechanism in which the two substrates are hydrogen-bonded to the boroxinate core in the enantiogenic step. The results of the Hammett study are supported by a computational study in which it is found that the H-O distance of the protonated imine hydrogen bonded to the anionic boroxinate core decreases with an increase in the electron releasing ability of the phenol unit incorporated into the boroxinate. The results are not consistent with a mechanism in which the boroxinate catalyst functions as a Lewis acid and activates the imine by a Lewis acid/Lewis base interaction.
Journal of Organic Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 623-50-7 belongs to class esters-buliding-blocks, and the molecular formula is C4H8O3, SDS of cas: 623-50-7 .
Referemce:
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