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    Structural Dynamics and Stereoselectivity of Chiral Benzylideneamine N,C‐Chelate Borane Photo–Thermal Isomerization

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    Date
    2020-01-03
    Author
    Novoseltseva, Polina
    Li, Haijun
    Wang, Xiang
    Sauriol, Francoise
    Wang, Suning
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    Abstract
    New chiral N,C-chelate organoboron compounds based on benzylideneamines (bza) with the general formula of B(bza-R)Mes2 (R=H or Me; Mes=mesityl) are reported. A chiral substituent group R- or S-CH(CH3)Ph (Ph=phenyl) was introduced to the imine center, which imposed a previously unobserved pseudo- or axial-chirality on the BMes2, creating distinct diastereomers. NMR spectroscopic studies established that the diastereomers undergo slow exchange in solution at ambient temperature. The chiral N,C-chelate B(bza-R)Mes2 molecules undergo photoisomerization in the same manner as their non-chiral analogues, generating chiral BN-cyclooctatriene (BN-COT) derivatives. Most significantly, by tracking the photoisomerization with circular dichroism (CD) and 1H?NMR spectra along with time-dependent density functional theory (TD-DFT) computational studies, the photoisomerization was established to proceed in a highly stereoselective manner, that is, one diastereomer converts exclusively to the corresponding diastereomer product in the photoreaction.
    URI for this record
    http://hdl.handle.net/1974/27742
    External DOI
    https://doi.org/10.1002/chem.201905312
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    • Department of Chemistry Faculty Publications
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