title: Stereoselective synthesis of azetidines and pyrrolidines from N-tert-butylsulfonyl(2-aminoalkyl)oxiranes.
abstract: Base-induced cyclization of enantiopure (2-aminoalkyl)oxiranes allowed the stereospecific formation of pyrrolidin-3-ols and/or 2-(hydroxymethyl)azetidines, depending on the reaction conditions. The oxidation of 2-(hydroxymethyl)azetidines led to azetidine-2-carboxylic acids in high yields.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.
authors.forename: Mohamed
authors.initials: M
authors.lastname: Medjahdi
authors.forename: José C
authors.initials: JC
authors.lastname: González-Gómez
authors.forename: Francisco
authors.initials: F
authors.lastname: Foubelo
authors.forename: Miguel
authors.initials: M
authors.lastname: Yus
mesh_terms: D001384:Azetidines / Q000737:chemistry*; D002082:Butylamines / Q000737:chemistry; D003500:Cyclization; D005027:Ethylene Oxide / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001384:Azetidines; D002082:Butylamines; D011759:Pyrrolidines; C005486:methylsulfonylbutylamine; D005027:Ethylene Oxide