Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution

Research output: Contribution to journalArticle

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Abstract

Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of ≥96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated β-lactams (±)-5 and (±)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (±)-7 and (±)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a, 5b, 6b and 8a with HCl/EtOH afforded the corresponding β-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s of ≥92%.

Original languageEnglish
Pages (from-to)2351-2358
Number of pages8
JournalTetrahedron Asymmetry
Volume12
Issue number16
DOIs
Publication statusPublished - Sep 13 2001

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Lactams
Enzyme kinetics
Enantiomers
enantiomers
Lipases
Lipase
enzymes
kinetics
Enzymes
synthesis
esters
Esters
rings
2-azetidinone

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of 4-aryl-substituted β-lactam enantiomers by enzyme-catalyzed kinetic resolution. / Forró, E.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 12, No. 16, 13.09.2001, p. 2351-2358.

Research output: Contribution to journalArticle

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