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Diastereoselective direct aldol reaction and subsequent cyclization of 2-azetidinone-tethered azides for the preparation of a 4-hydroxypipecolic acid analogue
* 1 , 2 , 1
1  Departamento de Química Orgánica I. Facultad de Química. Universidad Complutense de Madrid, 28040-Madrid, Spain
2  Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain

Abstract: The reaction of enantiopure 3-azido-4-oxoazetidine-2-carbaldehyde with acetone was catalyzed by L-proline, to give the corresponding aldol adduct. This product was stereocontrolled cyclized by using intramolecular reductive amination achieving a new 4-hydroxypipecolic acid analogue with a bicyclic b-lactam structure.