Synthetic studies of carbapenem and penem antibiotics. II. Synthesis of 3-acetyl-2-azetidinones by (2 + 2) cycloaddition of diketene and schiff bases

DOI: 10.1248/cpb.40.1094

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1094 - 1097 (1992)

Update date:2022-07-29

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Authors:

Sasaki Sasaki

Goda Goda

Enomoto Enomoto

Sunagawa

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Article abstract of DOI: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-azeti dinone, which is a key intermediate for the synthesis of carbapenem and penem antibiotics, were accomplished.

Full text of DOI:10.1248/cpb.40.1094

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