Domino Two-Step Oxidation of β-Alkoxy Alcohols to Hemiacetal Esters: Linking a Stoichiometric Step to an Organocatalytic Step with a Common Organic Oxidant

Tom Targel, Palakuri Ramesh, Moshe Portnoy

Research output: Contribution to journalArticlepeer-review

Abstract

Primary and secondary β-alkoxy alcohols can be cleanly and efficiently oxidized into hemiacetal esters in a cascade two-step process. mCPBA serves both as a stoichiometric oxidant in the first TEMPO-catalyzed step, converting alcohols to aldehydes/ketones, and as a reagent in the second Baeyer–Villiger stoichiometric oxidation, transforming the aldehydes/ketones into hemiacetal esters. The use of an oxidant common to both steps enables the domino reaction to proceed under a single experimental setting. Longer oxidative cascade sequences are possible when this new methodology is applied to suitable substrates.

Original languageEnglish
Pages (from-to)3017-3021
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number23
DOIs
StatePublished - 22 Jun 2018

Keywords

  • Domino reactions
  • Hemiacetal esters
  • Organocatalysis
  • Oxidation
  • Synthetic methods

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