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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
Published: 31 October 2009 by MDPI in The 13th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
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.