title: Highly diastereoselective synthetic route to enantiopure beta(2)-amino acids and gamma-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary.
abstract: The alkylation reactions of an amide enolate derived from a trifluoromethylated oxazolidine (Fox) chiral auxiliary occur with a complete diastereoselectivity and in good yields with various electrophiles. This reaction provides a versatile and straightforward strategy for the synthesis of beta(2)-amino acids and gamma-amino alcohols in enantiopure form.
authors.affiliation: Laboratoire Synthèse Organique Sélective et Chimie Organométallique (SOSCO), UMR CNRS 8123, Université de Cergy-Pontoise, Cergy-Pontoise Cedex, France.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Tessier
authors.forename: Nour
authors.initials: N
authors.lastname: Lahmar
authors.forename: Julien
authors.initials: J
authors.lastname: Pytkowicz
authors.forename: Thierry
authors.initials: T
authors.lastname: Brigaud
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000605:Amino Alcohols; D010080:Oxazoles; C064210:oxazolidine