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classificationIPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D417-06
http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D405-06
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filingDate 1986-09-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1990-08-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1990-08-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0218415-B1
titleOfInvention Process for intermediates to 1-carbapenems and 1-carbacephems
abstract A stereoselective process for chiral inter­mediates to 1-carbapenem and 1-carbacephalosporins is provided comprising the use of an N-acyl(4R)substituted-­1,3-thiazolidine-2-thione as a chiral auxiliary in boron enolate mediated aldol condensation with a protected-β-­keto ester aldehyde. Benzyl 3,3-(ethylenedioxy)-4-­formylbutyrate is condensed with the boron enolate formed with nbutyryl (4R)-methoxycarbonyl-1,3-thia­zolidine-2-thione to provide benzyl 3,3-ethylenedioxy-­(5R)-hydroxy-6-[(4R)-methoxycarbonyl-1,3-thiazolidine-­2-thione-3-ylcarbonyl]octanoate. Displacement of the thiazolidine-2-thione chiral auxiliary moiety with an O-alkyl, O-acyl or O-aralkyl hydroxyamine provides the corresponding chiral intermediate as the hydroxamate.
priorityDate 1985-09-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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