A Convenient Enantioselective Synthesis of (S)-alfa-Trifluoromethylisoserine

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Jiménez-Osés, G. 1
  4. Peregrina, J.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Zeitschrift:
Journal of Organic Chemistry

ISSN: 0022-3263

Datum der Publikation: 2005

Ausgabe: 70

Nummer: 14

Seiten: 5721-5724

Art: Artikel

DOI: 10.1021/JO0505371 PMID: 15989359 SCOPUS: 2-s2.0-22144478679 WoS: WOS:000230355200046 GOOGLE SCHOLAR

Andere Publikationen in: Journal of Organic Chemistry

Institutionelles Repository: lock_openOpen Access Editor

Zusammenfassung

This report describes two straightforward synthetic methodologies to obtain α-CF3-isoserine, a new α,α-disubstituted β-amino acid, from α-(trifluoromethyl)acrylic acid. The routes involve the synthesis of five-membered cyclic sulfates (using sulfuryl chloride) or sulfamidates (using the Burgess reagent) from the corresponding chiral diols, which are obtained by a catalytic asymmetric dihydroxylation (AD) reaction. © 2005 American Chemical Society.