ArticleStereoselective synthesis of the antibacterial 3-fluoro-d-alanine

Add time:08/14/2019    Source:sciencedirect.com

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 α-fluoro α′ -sulfinyl alcohol (2S,Rs)-1 under Mitsunobu conditions and the one-pot transformation of the N-Cbz α-sulfinyl amine (2R,Rs)-5 into the N-Cbz aminoalcohol (S)-7, through a “non-oxidative Pummerer reaction”.

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