Asymmetric Esterification for Total Synthesis

  • Author: Asian Journal of Organic Chemistry
  • Published Date: 04 November 2013
  • Source / Publisher: Asian Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Asymmetric Esterification for Total Synthesis

The condensation reaction of carboxylic acid and alcohol is known as esterification. This is one of the most fundamental transformations in organic chemistry, but an asymmetric version was not produced until recently, as reported by the team of Kenya Nakata, Shimane University, and Isamu Shiina, Tokyo University of Science, both Japan.

Kinetic resolution of racemic alcohols with achiral carboxylic acids in the presence of chiral nucleophilic organocatalysis by asymmetric esterification is a suitable method for the direct production of chiral carboxylic esters. To demonstrate the utility of the asymmetric esterification, the team applied it to the enantiodivergent synthesis of both enantiomers of centrolobine, which is an anti-inflammatory compound. Both (+)- and (–)-centrolobine (pictured) were successfully synthesized in a total of seven steps.

This new synthetic strategy will hopefully be applicable to the synthesis of other biologically active chiral compounds.

Article Views: 5661

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 and consult our permission guidance prior to making your request

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

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