HIGH STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS

PURPOSE:To obtain a beta-lactam which is used as a precursor for synthesizing carbapenem antibiotics by allowing an enolate to react with an imine derivative at room temperature in high stereoselectivity in high yield, producing only one cis-isomer. CONSTITUTION:A beta-hydroxybutyric acid ester such...

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Bibliographic Details
Main Author KOKUNI NOBUKI
Format Patent
LanguageEnglish
Published 18.07.1989
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:PURPOSE:To obtain a beta-lactam which is used as a precursor for synthesizing carbapenem antibiotics by allowing an enolate to react with an imine derivative at room temperature in high stereoselectivity in high yield, producing only one cis-isomer. CONSTITUTION:A beta-hydroxybutyric acid ester such as methyl (R)-beta- hydroxybutyrate is allowed to react with a dialkylzinc of the formula ZnR2 (R is alkyl) in a solvent such as tetrahydrofuran to form an alkylzinc alcoholate, then allowed to react with lithium diisopropylamide, etc., to give an enolate of formula I (R is lower alkyl; R is alkyl, aryl; M is Zn, alkali metal). The enolate is allowed to react with an imine derivative of formula II (R is aro matic group; R is trialkylsilyl, alkylarylsilyl) in an inert gas at room tempera ture to give the subject compound of formula III, stereoselectively only the cis-form.
Bibliography:Application Number: JP19880001559