One Method, Four Enantiomers

  • ChemPubSoc Europe Logo
  • Author: Asian Journal of Organic Chemistry
  • Published Date: 24 May 2014
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: One Method, Four Enantiomers

β-Lactams are one of the basic skeletons of antibiotics and have been clinically used since the 1940s. Penicillin, cephalosporin, thienamycin, and 1β-methyl carbapenem are the representative examples of β-lactam antibiotics. As the stereochemistry of the substituents at the 3 and 4 positions of the β-lactam ring affects the bioactivity, numerous methods for the stereocontrolled synthesis of 3,4-cis- and trans-substituted β-lactams have been attempted. Among them, a stereoselective synthesis of these isomers from a single precursor is highly desired.


Makoto Shimizu and co-workers, Mie University, Japan, developed a highly enantioselective synthesis of both 3,4-cis- and trans-β-lactams by the reduction of iminocyclobutenones catalyzed by a chiral phosphoric acid followed by thermal rearrangement of the resulting aminocyclobutenones. This chiral β-lactam synthesis is particularly attractive because four possible enantiomers of 3,4-disubstituted β-lactams can be synthesized from a single iminocyclobutenone by using both enantiomers of the chiral phosphoric acid catalyst in the enantioselective reduction and appropriate amines in the subsequent thermal rearrangement reaction.


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