On the mechanism and stereochemistry of the formation of β-lactam derivatives of 2,4-disubstituted-2,3-dihydro-benzo[1,4]diazepines

2-Chloro-4-phenyl-2a-(4′-methoxyphenyl)-3,5-dihydroazatetracyclic [1,2-d]benzo [ 1,4]diazepin-1 -one (IIIa) and 2-chloro-4-methyl-2a-(4′-methoxyphenyl)-3,5-dihydroazatetracyclic[1,2-d]-benzo[1,4]diazepin-1-one (IIIb) were synthesized. 1-Benzoyl-2-phenyl-4-(4′-methoxyphenyl)[1,4]-benzodiazepine (IIa) was formed through benzoylation of starting material 2-phenyl-4-(4′-methoxyphenyl)-[1,4]benzodiazepine (Ia) with the inversion of seven-member ring boat conformation. The thus formed β-lactams should have four pairs of stereoisomers. However, only one pair of enantiomers (2S,2R,4R) and (2R,2aS,4S) was obtained. The mechanism and stereochemistry of the formation of these compounds were studied on the basis of nmr spectroscopy and further confirmed by X-ray diffraction.