Literature DB >> 25560883

Straightforward synthesis of novel enantiopure α-trifluoromethylated azetidine 2-carboxylic acid and homoserines.

Nathalie Lensen1, Joyce Marais, Thierry Brigaud.   

Abstract

The straightforward syntheses of enantiopure (2R)-2-trifluoromethyl-2-carboxyazetidine and (R)- and (S)-trifluoromethylhomoserines are reported. The key step is a Strecker-type reaction on a common chiral CF3-containing bicyclic oxazolidine intermediate obtained by a condensation reaction of (R)-phenylglycinol and ethyl-4,4,4-trifluoroacetoacetate (ETFAA).

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Year:  2015        PMID: 25560883     DOI: 10.1021/ol503448w

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  2 in total

Review 1.  CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

Authors:  Anthony J Fernandes; Armen Panossian; Bastien Michelet; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
Journal:  Beilstein J Org Chem       Date:  2021-02-03       Impact factor: 2.883

2.  Trifluoromethylated proline analogues as efficient tools to enhance the hydrophobicity and to promote passive diffusion transport of the l-prolyl-l-leucyl glycinamide (PLG) tripeptide.

Authors:  Martin Oliver; Charlène Gadais; Júlia García-Pindado; Meritxell Teixidó; Nathalie Lensen; Grégory Chaume; Thierry Brigaud
Journal:  RSC Adv       Date:  2018-04-18       Impact factor: 4.036

  2 in total

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