title: Straightforward synthesis of novel enantiopure α-trifluoromethylated azetidine 2-carboxylic acid and homoserines.
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).
authors.affiliation: Laboratoire de Chimie Biologique (LCB), EA 4505, Université de Cergy-Pontoise , 5 Mail, Gay-Lussac, Neuville sur Oise, 95000 Cergy-Pontoise Cedex, France.
authors.forename: Nathalie
authors.initials: N
authors.lastname: Lensen
authors.forename: Joyce
authors.initials: J
authors.lastname: Marais
authors.forename: Thierry
authors.initials: T
authors.lastname: Brigaud
mesh_terms: D000090:Acetoacetates / Q000737:chemistry*; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001383:Azetidinecarboxylic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006714:Homoserine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000600471:2-trifluoromethyl-2-carboxyazetidine; D000090:Acetoacetates; D000605:Amino Alcohols; D001384:Azetidines; D010080:Oxazoles; C523790:ethyl 4,4,4-trifluoroacetoacetate; C064210:oxazolidine; D001383:Azetidinecarboxylic Acid; D006714:Homoserine