Structural and electronic effects of oxazolidine ligands derived from (1R,2S)-ephedrine in the asymmetric addition of diethylzinc to aldehydes |
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Authors: | Ewelina Błocka Magdalena Jaworska Anna Kozakiewicz Mirosław Wełniak Andrzej Wojtczak |
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Affiliation: | 1. Department of Organic Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Toruń, Poland;2. Department of Crystallochemistry and Biocrystallography, Nicolaus Copernicus University, Gagarina 7, 87-100 Toruń, Poland |
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Abstract: | The purpose of this research was to determine the activity of chiral oxazolidine ligands prepared from (1R,2S)-ephedrine for the enantioselective addition of diethylzinc to aldehydes. The configuration on the newly formed C2 stereogenic center was determined as (2S) by X-ray structural analysis. Oxazolidine ligands reveal medium enantioselectivity with the ee exceeding 57%, and the yields obtained being 68–99%. The results indicate that the absolute configuration of the addition product depends not only on the N3-methyl as an important stereocontrol element but also on both the electronic and steric effects of the substrates and oxazolidine ligands. |
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