Stereoselective synthesis of trifluoromethyl-substituted 1,2-diamines by aza-Michael reaction with trans-3,3,3-trifluoro-1-nitropropene |
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| Authors: | Joë l Turconi,Jean-Marc Paris |
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| Affiliation: | a Laboratoire de Synthèse Bioorganique associé au CNRS, Université Louis Pasteur de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 24, 67401 Illkirch Cedex, France
b Rhodia Recherches, Centre de Recherches et de Technologies de Lyon, 85 avenue des Frères Perret, BP 62, 69192 Saint-Fons Cedex, France |
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| Abstract: | Aza-Michael addition of optically pure 4-phenyl-2-oxazolidinone to 3,3,3-trifluoro-1-nitropropene proceeds smoothly at low temperature with a high yield. Diastereoselectivity of the addition depends on the base used and lithiated species proved to be highly efficient affording 92% de. Optically pure 1,2-diamino-3,3,3-trifluoropropane is prepared in 58% yield from the aza-Michael addition product through a three-step procedure. |
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| Keywords: | Perfluoroalkyl nitroalkene Diastereoselective aza-Michael addition 3,3,3-Trifluoro-1-nitropropene 4-Phenyl-2-oxazolidinone |
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