A carbon–carbon bond formation reaction at the C-4 position of a β-lactam
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1884-1887
- https://doi.org/10.1039/p19810001884
Abstract
Upon treatment with various organolithiums, 4-acetoxyazetidin-2-one (10) afforded the corresponding carbondisplaced compounds (11), (12), and (13). 4-(3-Diazo-3-ethoxycarbonyl-2-oxopropyl)azetidin-2-one (15) was also synthesised from (10) and ethyl α-diazoacetoacetate in the presence of lithium hexamethyldisilazide in one step. The diazo-compound (15) was thermally cyclised to the bicyclic keto-ester (17) in the presence of rhodium acetate.Keywords
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