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Synthesis 2002(17): 2589-2596
DOI: 10.1055/s-2002-35632
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

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

Natalie A. Fokina*, Andrei M. Kornilov, Irina B. Kulik, Valery P. Kukhar
Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Science of Ukraine, Murmanskaya 1, Kiev, 02094, Ukraine
Fax: +38(044)5732552; e-Mail: natfokina@yahoo.com;
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Publication History

Received 16 September 2002
Publication Date:
20 November 2002 (online)

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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.

Key words

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