Asymmetric Synthesis of Carbapenems Using Chiral Acetals: Synthesis of a Key Intermediate to (+)-PS-5

Abstract
Coupling reaction of the chiral imine acetal 5 [(4S,5S)-4,5-bis (methoxymethyl)-2- [(4-methoxyphenylimino)methyl]-2-(3-methoxyphenyl)-1, 3-dioxolane] and lithium enolate of methyl acetate proceeded in a highly diastereoselective manner to give ß-lactam 6. The reaction was applied to the synthesis of a key intermediate 11 [(2S,3R)-3-ethyl-4-oxo-2-azetidineacetic acid] to (+)-PS-5.

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