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Asymmetric synthesis of α,α-difluoro-β-amino phosphonic acids using sulfinimines |
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| Authors: | Gerd-Volker Röschenthaler Valery Kukhar Natalia Gvozdovska Alexander Sorochinsky |
| Institution: | a Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Strasse, 28334 Bremen, Germany b Institute of Bioorganic Chemistry & Petrochemistry, NAS of Ukraine, Murmanska 1, Kiev-94, 02660, Ukraine c Hansa Fine Chemicals GmbH, Leobener Strasse, 28334 Bremen, Germany |
| Abstract: | Addition of diethyl lithiodifluoromethylphosphonate to enantiopure sulfinimines afforded the corresponding N-sulfinyl α,α-difluoro-β-amino phosphonates with good diastereoselectivity. A two-step deprotection involving treatment of diastereomerically pure N-sulfinyl α,α-difluoro-β-amino phosphonates with trifluoroacetic acid in EtOH followed by refluxing with 10 N HCl afforded enantiopure α,α-difluoro-β-amino phosphonic acids. |
| Keywords: | Asymmetric synthesis Amino phosphonic acids and derivatives Fluorine and compounds Sulfinimines Diethyl difluoromethylphosphonate |
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