Literature DB >> 20481551

Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines.

Grégory Chaume1, Olivier Barbeau, Philippe Lesot, Thierry Brigaud.   

Abstract

Trifluoromethyl group containing oxazolidines (Fox) are conveniently synthesized by condensation of serine esters with trifluoroacetaldehyde hemiacetal or trifluoroacetone. These oxazolidines can undergo N-acylation and amidification reactions and are completely configurationally and hydrolytically stable. Therefore, they can be considered as highly valuable proline surrogates (Tfm-pseudoprolines).

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Year:  2010        PMID： 20481551     DOI： 10.1021/jo100518t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 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

3.  cis-trans-Amide isomerism of the 3,4-dehydroproline residue, the 'unpuckered' proline.

Authors:  Vladimir Kubyshkin; Nediljko Budisa
Journal:  Beilstein J Org Chem       Date:  2016-03-29       Impact factor: 2.883
  3 in total

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