Chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams from ethylbromodifluoroacetate and imines during Reformatsky reaction |
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| Authors: | Nicolas Boyer Guillaume De Nanteuil Jean-Charles Quirion |
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| Institution: | a UMR CNRS 6014, Institut de Recherche en Chimie Organique Fine, INSA et Université de Rouen, 1 rue Tesnière, 76131 Mont-Saint-Aignan Cedex, France
b Division D of Medicinal Chemistry, Institut de Recherches Servier, 11 rue des Moulineaux, 92150 Suresnes, France |
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| Abstract: | The chemoselective and stereoselective synthesis of gem-difluoro-β-aminoesters or gem-difluoro-β-lactams was investigated from ethylbromodifluoroacetate and imines during Reformatsky reaction. Influence of various reaction parameters, such as nature of the amine part, nature of the chiral auxiliary, was evaluated. High levels of stereoselectivity (up to 98%) were obtained for gem-difluoro-β-aminoesters and gem-difluoro-β-lactams using either (R)-phenylglycinol or (R)-methoxyphenylglycinol. |
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| Keywords: | Reformatsky reaction Difluoro-β-aminoesters Difluoro-β-lactams (R)-Methoxyphenylglycinol |
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