Convenient synthesis of trans-beta-amino carboxylic esters with an azetidine skeleton via rearrangement of beta,gamma-aziridino alpha-amino esters.
A short and facile approach to biologically interesting N-protected alkyl 3-aminoazetidine-2-carboxylic esters, a new class of conformationally restricted beta-amino esters, was developed. Reduction of anti-beta,gamma-aziridino-alpha-(N-diphenylmethylidene)amino esters and subsequent regioselective intramolecular ring opening of the beta,gamma-aziridine ring via nucleophilic attack of the alpha-amino function afforded the trans-azetidines.
Kiss
Loránd
L
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
Mangelinckx
Sven
S
Fülöp
Ferenc
F
De Kimpe
Norbert
N
D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism
D001384:Azetidines; D002264:Carboxylic Acids; D004952:Esters; C082735:azetidine