Synthesis of beta-lactams from azetidine carboxylic acid esters

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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2603407, 2603409R, 2603303, 26032613B, 260687R, C07D20508, C07D40306, C07D40906, C07D40706

Patent

active

041905792

ABSTRACT:
Azetidine carboxylic acid esters are converted into enol silyl ethers which, as enamino ketene acetals, undergo ready oxidative cleavage of the ethylenically unsaturated double bond, e.g. by dye-sensitized photo-oxygenation, to form beta-lactams. The beta-lactams and substitution products thereof are useful intermediates in the synthesis of biologically active lactams.

REFERENCES:
Foote et al., Tet. Letters 1968, pp. 3267-3270.
Haber, Tet. Letters, 1968, pp. 3271-3272.
Foote et al., Tet. Letters, 1975, pp. 1247-1250.

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