کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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42784 | 45941 | 2009 | 9 صفحه PDF | دانلود رایگان |
Purpose of the research was to determine the activity of chiral imine ligands prepared from (1S,2R)-norephedrine for the enantioselective addition of diethylzinc to aldehydes. Imine ligands reveal medium enantioselectivity, with the ee exceeding 30%. The highest ee (97%) was obtained for imine with 9-anthryl substituent, when p-methoxybenzaldehyde was used as substrate. The yields of the reaction obtained after 24–72 h reached 76–96%. The absolute configuration of the addition product depends on the geometry of presented transition states and π–π stacking interactions between the investigated ligands and the benzaldehyde substrate. Imine ligands derived 2-hydroxyacetophenone and with 9-anthryl substituent reveal strong absorbance in UV–vis spectra. Intermediates for the imines – diethylzinc – based catalysis and probable mechanisms were proposed.
A series of chiral imine ligands was prepared from (1S,2R)-norephedrine and applied for the enantioselective addition of diethylzinc to aldehydes. The absolute configuration of the addition product depends on the imine's nitrogen substituent. The highest ee (97%) was observed for imine with 9-anthryl substituent, when applied for p-methoxybenzaldehyde as substrate. Imine ligands derived 2-hydroxyacetophenone and with 9-anthryl substituent reveal strong absorbance in UV–vis spectra. Intermediates for the imines – diethylzinc – based catalysis and probable mechanisms were proposed.Figure optionsDownload as PowerPoint slide
Journal: Applied Catalysis A: General - Volume 357, Issue 2, 15 April 2009, Pages 150–158