Synthesis of 2-trifluoromethyl-1,3-oxazolidines as hydrolytically stable pseudoprolines.
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).
Chaume
Grégory
G
Laboratoire SOSCO, Université de Cergy-Pontoise, 5 Mail Gay-Lussac, Neuville sur Oise, 95000 Cergy-Pontoise cedex, France.
Barbeau
Olivier
O
Lesot
Philippe
P
Brigaud
Thierry
T
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*
D004952:Esters; D010080:Oxazoles; D013844:Thiazoles; C505976:pseudoproline; C064210:oxazolidine; D005461:Fluorine; D011392:Proline; D008697:Methane