One Method, Four Enantiomers

  • 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.

Article Views: 3556

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

Follow on Facebook Follow on Twitter Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH