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Chemical and Pharmaceutical Bulletin
Vol. 40 (1992) No. 5 P 1094-1097

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http://doi.org/10.1248/cpb.40.1094


It was found that (2+2) cycloaddition reaction of diketene with Schiff bases was effectively promoted by imidazole as a catalyst to afford 3-acetyl-2-azetidinone derivatives 4. As an application of this new method, a practical asymmetric synthesis of 4 and its conversion into (3S, 4S)-4-carboxy-1-(di-p-anisylmethyl)-3-[(R)-1-hydroxyethyl]-2-azetidinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, were accomplished.

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