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EnglishThe wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd.
http://hdl.handle.net/11697/11276| Titolo: | Stereoselective Synthesis of the Antibacterial 3-Fluoro-D-Alanine |
| Autori interni: | CRUCIANELLI, MARCELLO |
| Data di pubblicazione: | 1997 |
| Rivista: | TETRAHEDRON-ASYMMETRY |
| Abstract: | The wide spectrum antibacterial 3-fluoro-D-alanine (S)-9 has been stereoselectively synthesized via ''chiral sulfoxide chemistry''. Key steps are the azidation of the alpha-fluoro alpha'-sulfinyl alcohol (2S,R-s)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz alpha-sulfinyl amine (2R,R-s)-5 into the N-Cbz aminoalcohol (S)-7, through a ''non-oxidative Pummerer reaction''. (C) 1997 Published by Elsevier Science Ltd. |
| Handle: | http://hdl.handle.net/11697/11276 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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