Synthesis of C2-symmetrical chiral diamines: diastereoselective addition to bis(1,3-oxazolidinyl)alkanes with Grignard reagents |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Engineering, Muroran Institute of Technology, Muroran, Hokkaido 050-8585, Japan;2. Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan;3. Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, 2-2-1 Katahira, Aoba-ku, Sendai 980-8577, Japan;4. Tokiwakai Group, 62 Numajiri, Tsuzura-cho, Uchigo, Iwaki, Fukushima 973-8403, Japan;1. Department of Physical Chemistry and Department “Science and Technology of Life, Light and Matter”, University of Rostock, Dr-Lorenz-Weg 1, Rostock D-18059, Germany;2. Department of Physical Chemistry, Kazan Federal University, Kremlevskaya str. 18, 420008 Kazan, Russia;1. Institute of Organic Chemistry, National Academy of Sciences of the Ukraine, Murmanskaya St., 5, UA-02094, Kyiv, Ukraine;2. Department of Chemistry, Taras Shevchenko National University of Kyiv, 64/13, Volodymyrska Str. Kyiv, 01601, Ukraine;3. The Chemours Company, 200 Powder Mill Rd., Experimental Station Wilmington, DE, 19803, USA |
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| Abstract: | Asymmetric syntheses of C2-symmetrical chiral 1,4- and 1,5-diamines with stereogenic centers adjacent to the nitrogen atom have been accomplished. Chiral diamines were prepared by diastereoselective alkylations of bisoxazolidine, which was derived from (R)-phenylglycinol. Methyl and phenyl Grignard reagents were employed as alkylating reagents. In addition, tertiary chiral diamines were readily converted to primary diamines in high yield. |
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