Synthesis of 4-oxo-2-azetidineacetic acids by means of radical cyclization of N-vinylic α-bromo amides

Add time:07/15/2019    Source:sciencedirect.com

Bu3SnH-mediated radical cyclization of α-bromo amide 8, bearing phenyl and phenylthio substituents at the terminus of the N-vinylic bond, proceeded in a 4-exo-trig manner to give β-lactam 9. Ruthenium tetroxide oxidation of the phenyl group incorporated into the product 9 provided a new synthesis of 4-oxo-2-azetidineacetic acid 13, a usuful intermediate for (±)-PS-5. Chiral 4-oxo-2-azetidineacetic acids 23 and 36, key intermediates for the synthesis of (+)-PS-5 and (+)-thienamycin, respectively, were also obtained through the asymmetric radical cyclization of N-vinylic α-bromo amides having chiral auxiliaries at the side chain.

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