Photolysis of α-diazo N-methoxy-N-methyl (Weinreb) β-ketoamides derived from enantiomerically pure (EP) α-amino acids affords the corresponding EP β-lactam via an intramolecular Wolff rearrangement. Photochemistry is promoted with either standard UV irradiation or through the use of a 100W compact fluorescent light (CFL); the latter affords a safe and environmentally friendly alternative to standard photolysis conditions. A continuous-flow photochemical reactor, made from inexpensive laboratory equipment, expedites reaction times and is amenable to scale-up. Diastereoselectivity (cis or trans) of the product β-lactams has been shown to vary from modest to nearly complete. An extremely facile, atom-economical method for the epimerization of the product mixture to the trans isomer, generally highly crystalline, has been developed. Evidence is presented for C-3 epimerization of Weinreb amide structures via a non-basic, purely thermal route. Subsequent transformations of both the Weinreb amide at C-3 (β-lactam numbering) and amino acid side chain at C-4 are well tolerated, allowing for a versatile approach to diverse β-lactam structures. The technology is showcased in the synthesis of a common intermediate used toward several carbapenem-derived structures starting from unfunctionalized aspartic acid.