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Communication | Regular issue | Vol 14, No. 5, 1980, pp.575-578
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0575
A New Carbon-Carbon Bond Formation Reaction at the C-4 Position of a β-Lactam

Tetsuji Kametani,* Toshio Honda, Junko Sasaki, Hirofumi Terasawa, Yoshito Nakayama, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Reaction of 4-acetoxy-2-azetidinone (1) with various organolithiums gave the corresponding C-4 substituted compounds (2), (3), and (5). Treatment of 1 with bromoacetaldehyde diethyl acetal in the presence of magnesium afforded 4-ethoxy-2-azetidinone (6) as the only product.