期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 79, 期 20, 页码 9455-9464出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo500982j
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资金
- State Key Lab of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
In this study, a series of mono- and dialkylated chiral 1,2amino phosphinamide ligands derived from modular (1R,2R)-diphenylethylenediamine were successfully applied in the chiral 1,2-amino phosphinamide-Zn(II) catalyzed asymmetric Henry reaction between benzaldehyde and nitromethane. Although the chiral N-monosubstituted and N,N-disubstituted 1,2-amino phosphinamide ligands gave the main alcohol products with opposite configurations, a validated quantitative structure activity relationship (QSAR) mathematical model could be constructed between the physical Sterimol steric parameters of the Nsubstituents of the chiral ligands and the enantiomeric ratios of the alcohol products produced in the asymmetric Henry reaction. Since two sets of Nsubstituents are involved in the QSAR model construction, the key factor to succesfully construct a highly correlative and predictive model is to appropriately assign the N-substitutents. Ligand optimization based on the established phosphinamide ligand 2r, which produced (R)-beta(-)nitroalcohol in excellent yield and enan addition, a quantitative correlation could also be established with the use of subtractive QSAR model led to chiral 1,2-amino tioselectivity (99% yield and 92% ee). In Sterimol parameters.
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