Constructive Ozonolysis: Capturing Primary Ozonides

10 October 2022, Version 1

Abstract

Ozonolysis is a widely used and practical synthetic technique for the deconstructive oxidation of olefins using ozone. While there are numerous ozonolysis reactions that give myriad products and functionality, almost all of them involve scission at the olefin double bond. Utilizing ozone as a constructive reagent rather than a deconstructive one would open new domains of chemical reactivity and amplify molecular complexity in synthetic methodology. We report here the first instance of primary ozonides as preparative synthetic intermediates for a safe and green olefin syn-dihydroxylation reaction. Additionally, we have demonstrated this method using a continuous flow reactor that virtually eliminates peroxide accumulation and extended these applications towards the synthesis of pharmaceutically relevant small molecules including guaifenesin, the active ingredient in Mucinex and a precursor to ponesimod, a drug to treat multiple sclerosis.

Content

Supplementary materials

Supplementary Materials
All data are available in the main text or the supplementary materials.

Comments

Comments are not moderated before they are posted, but they can be removed by the site moderators if they are found to be in contravention of our Commenting Policy [opens in a new tab] - please read this policy before you post. Comments should be used for scholarly discussion of the content in question. You can find more information about how to use the commenting feature here [opens in a new tab] .
This site is protected by reCAPTCHA and the Google Privacy Policy [opens in a new tab] and Terms of Service [opens in a new tab] apply.