Lactic acid derived aziridinyl alcohols as highly effective catalysts for asymmetric additions of an organozinc species to aldehydes |
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Authors: | Stanisław Leśniak Michał Rachwalski Szymon Jarzyński Emilia Obijalska |
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Affiliation: | Department of Organic and Applied Chemistry, University of ?ód?, Tamka 12, 91-403 ?ód?, Poland |
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Abstract: | A straightforward synthetic route to a series of new catalysts bearing secondary hydroxyl and aziridine moieties as nucleophilic centers built on the chiral skeleton of (S)-(+)-lactic acid is described. All of the new compounds have been tested in the enantioselective addition of diethyl- and phenylethynylzinc to aryl and alkyl aldehydes, yielding the corresponding chiral alcohols in high chemical yields (up to 85%) and good ee’s of approximately 85%. The influence of the stereogenic center located at the aziridine subunit on the stereochemical outcome is also discussed. |
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