Stereoselective synthesis of azetidines and pyrrolidines from N-tert-butylsulfonyl(2-aminoalkyl)oxiranes.
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.
Medjahdi
Mohamed
M
Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain.
González-Gómez
José C
JC
Foubelo
Francisco
F
Yus
Miguel
M
D001384:Azetidines / Q000737:chemistry*; D002082:Butylamines / Q000737:chemistry; D003500:Cyclization; D005027:Ethylene Oxide / Q000737:chemistry*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D001384:Azetidines; D002082:Butylamines; D011759:Pyrrolidines; C005486:methylsulfonylbutylamine; D005027:Ethylene Oxide