Towards Optically Pure Mono- and Difluorinated Amino Acids: Common Methodology­ Based on (R)-2,3-O-Isopropylideneglyceraldehyde

Abstract

The stereocontrolled synthesis of N-protected (2S,3R)-2-amino-3-fluoroundecanoic and (3R)-3-amino-2,2-difluoroundecanoic acids, as representative examples, from commercially available optically pure (R)-2,3-O-isopropylideneglyceraldehyde is described. Key steps involve the Mitsunobu reaction for the introduction of amino function, and incorporation of fluorine atom(s) by the fluorinating agent, morpholinotrifluorosulfurane.

nucleophilic fluorination - 1,2-diols - the Mitsunobu reaction - protecting group - fluorine-containing amino acids

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