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Reaction of 4-acetoxy-2-azetidinone with tertiary carbanions: Preparation of 4-alkyl- and 4-alkylidene-2-azetidinones

✍ Scribed by C.W. Greengrass; D.W.T. Hoople

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 198 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)90264-3

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✦ Synopsis

Reaction of 4-acetoxy-2-azetidinone with tertiary stabilised carbanions gives carbonsubstituted 2-azetidinones which have been transformed into 4-alkylidene-2-azetidinones. The discovery of naturally occuring carbapenem antibiotics has prompted a search for analogue synthesis. Although many 2-azetidinones bearing carbon substituents at C(4) are known' 2 there are few reports of carbon-carbon bond formation at C(4) and no high-yielding transformations of this type using N-unsubstituted 2-azetidinones have been described.+ The

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