title: Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines.
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).
authors.affiliation: Laboratoire SOSCO, Université de Cergy-Pontoise, 5 Mail Gay-Lussac, Neuville sur Oise, 95000 Cergy-Pontoise cedex, France.
authors.forename: Grégory
authors.initials: G
authors.lastname: Chaume
authors.forename: Olivier
authors.initials: O
authors.lastname: Barbeau
authors.forename: Philippe
authors.initials: P
authors.lastname: Lesot
authors.forename: Thierry
authors.initials: T
authors.lastname: Brigaud
mesh_terms: D000215:Acylation; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D004952:Esters; D010080:Oxazoles; D013844:Thiazoles; C505976:pseudoproline; C064210:oxazolidine; D005461:Fluorine; D011392:Proline; D008697:Methane