J. Podlech, STEREOSELECTIVE SYNTHESIS OF AMINOALKYL-SUBSTITUTED BETA-LACTAMS VIA CYCLOADDITION OF KETENES GENERATED FROM ALPHA-AMINO-ACIDS, Synlett, (6), 1996, pp. 582
Photochemical rearrangement of diazoketones 1 - 8 (derived from suitab
ly protected alpha-amino acids) in the presence of imines led to the d
iastereoselective formation of aminoalkyl-substituted beta-lactams 10
- 17. The two diastereoisomeric trans-substituted ring systems were fo
rmed with selectivities up to 93:7 and yields up to 90 %.