Abstract

Stereoselective aldol condensation of a 4, 5-diphenyl-oxazolin-2-one (Ox) glycine provided α-amino- β-hydroxy acid 4, which, after coupling with phenylglycine derivatives, was directly cyclized to β lactams. Ozonolysis cleaved both the Ox and isopropylidene groups and initiated a Chapman rearrangement to the corresponding α-benzamido-β-acyl-2 azetidinone 8. Subsequent reduction induced a diastereoselective rearrangement to the corresponding γ-lactone 13.

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