184871-53-2

Upstream product

• 184871-52-1 (3R,4R)-3-Ethyl-4-(3-methoxy-benzyl)-1-((S)-1-phenyl-ethyl)-azetidin-2-one 
• 35553-92-5 ETHYL 3-METHOXYPHENYLACETATE 
• 184871-48-5 (3-Methoxy-phenyl)-phenylsulfanyl-acetaldehyde 
• 184871-46-3 (3-Methoxy-phenyl)-phenylsulfanyl-acetic acid ethyl ester 

Downstream Products

• 140169-06-8 (3R,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-ethyl-4-(3-methoxy-benzyl)-azetidin-2-one 
• 141195-51-9 (3R,4R)-4-(benzyloxycarbonylmethyl)-1-(tert-butyldimethylsilyl)-3-ethylazetidin-2-one 
• 141195-52-0 (3R,4R)-4-(benzyloxycarbonylmethyl)-3-ethylazetidin-2-one 

Relevant academic research and scientific papers

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

Bu2SnH-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 useful 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 auxillaries at the side-chain.