A practical and efficient method for the resolution of 3‐phospholene 1‐oxides via coordination complex formation1 |
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| Authors: | Viktória Ujj Péter Bagi József Schindler János Madarász Elemér Fogassy György Keglevich |
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| Institution: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H‐1521 Budapest, Hungary;2. Research Group of the Hungarian Academy of Sciences at the Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H‐1521 Budapest, Hungary;3. Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, H‐1521 Budapest, Hungary |
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| Abstract: | A simple, efficient, and economical method based on the combination of the exceptional behavior of o,o′‐dibenzoyl‐ or o,o′‐di‐p‐toluyl‐(2R,3R)‐tartaric acid in chiral recognition processes, and the coordination ability of calcium or magnesium ion was developed for the resolution of phospholene oxides 1 . The calcium or magnesium salt of (?)‐o,o′‐dibenzoyl‐(2R,3R)‐tartaric acid 2 , 4 ‐ 6 or calcium hydrogen (?)‐o,o′‐di‐p‐toluyl‐(2R,3R)‐tartrate 3 may form crystalline diastereomeric coordination complexes with the appropriate antipode of substituted 3‐phospholene oxides 1 that makes possible efficient resolutions. Optically active phospholene oxides 1 were prepared directly by simply crystallization and digestion of the corresponding diastereomeric complexes so formed. Thermal behavior of the crystalline diastereomeric complexes was studied by simultaneous TG/DTA. The novel method may be of more general value in respect of the resolution of tertiary phosphine oxides. Chirality, 2010. © 2010 Wiley‐Liss, Inc. |
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| Keywords: | coordinative resolution P‐chiral phospholene oxides tartaric acid derivatives solvent dependence |
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