Diastereoface-Differentiating Synthesis of Substituted β-Lactams from Chiral Imines and/or Chiral α-Chloro Iminium Chlorides

Article abstract of DOI:10.1021/jo00182a015

Reaction of imines carrying a chiral substituent at a nitrogen atom with symmetric or prochiral α-chloro iminium chlorides leads in a diastereoface-differentiating reaction to a mixture of diatereoisomeric or epimeric β-lactams.Attempts were made to determine the absolute configuration of obtained chiral β-lactams.Reaction of prochiral imines with chiral α-chloro iminium chlorides also provides mixtures of diastereomeric β-lactams or their enantiomers with a clear selectivity.