Diastereoselective synthesis of 2-substituted-piperidin-4-ones as convenient precursors for an asymmetric approach to carbacephams

Optically active carbacephams can be efficiently prepared generating the β-lactam ring on 2-substituted-piperidin-4-ones. These can, in turn, be prepared diastereoselectively through a Michael–Michael reaction sequence initiated by benzylamine on precursors derived by Wittig reaction between serinals and 4-[(4-methylphenyl)sulfonyl]-1-(triphenylphosphoranylidene)-2-butanone.