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.
Stereoselective Synthesis of the Antibacterial 3-Fluoro-D-Alanine
CRUCIANELLI, MARCELLO;
1997
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.File in questo prodotto:
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