Stereoselective addition of dialkyl phosphites to di-salicylaldimines bearing the (R,R)-1,2-diaminocyclohexane moiety |
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Authors: | Jarosław Lewkowski Paweł Tokarz Tadeusz Lis Katarzyna Ślepokura |
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Affiliation: | 1. Department of Organic Chemistry, Faculty of Chemistry, University of ?ód?, Tamka 12, 91-403 ?ód?, Poland;2. Faculty of Chemistry, University of Wroc?aw, F. Joliot-Curie 14, 50-383 Wroc?aw, Poland |
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Abstract: | The addition of dialkyl phosphites to the azomethine bond of N,N′-disalicylidene-1,2-diaminocyclohexane imines, catalyzed by sodium hydride led to bis-aminophosphonates in a high diastereoselectivity. One of the bis-aminophosphonates was analyzed by X-ray diffraction. Another bis-aminophosphonate was converted to a bis-aminophosphonic acid and the structure was studied by X-ray diffraction. Addition of phosphites to a diimine resulted in an aminophosphonate, which was also studied by X-ray diffraction. An explanation of the diastereoselectivity is suggested. |
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Keywords: | Aza-Pudovik reaction Stereoselectivity 1,2-Diaminocyclohexane Aminophosphonates |
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