Tetrahedron p. 1703 - 1712 (1985)
Update date:2022-09-26
Topics:
Arrieta
Cossio
Palomo
The development of a practical method for the preparation of vinylamino-β-lactams from Dane salts and Schiff bases is described. Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino-β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead of β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the starting Schiff bases provides a convenient route to the corresponding β-lactams instead of oxazolidines. Some observations on the scope of the method are made.
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Doi:10.1248/cpb.30.3065
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(1986)