Acyloin Coupling Reactions

K. A. Scheidt*, E. A. O'Bryan

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter

11 Scopus citations

Abstract

The α-hydroxy ketone group, or acyloin, is prevalent in natural products and pharmaceuticals, and the development of efficient methods to install this functional group remains an important synthetic challenge. As a result, several distinct methods for the synthesis of α-hydroxy ketones have been developed. This chapter presents a review of approaches toward this structural motif in which the acyloin is derived from the coupling of two carbonyl units to form a new carbon-carbon σ-bond. This definition encompasses the traditional acyloin condensation, involving the reductive coupling of two aliphatic esters, and recent catalytic approaches that invoke acyl anion intermediates (umpolung reactivity).

Original languageEnglish (US)
Title of host publicationComprehensive Organic Synthesis
Subtitle of host publicationSecond Edition
PublisherElsevier Ltd
Pages621-655
Number of pages35
Volume3
ISBN (Print)9780080977430
DOIs
StatePublished - Feb 2014

Keywords

  • Acyl anion equivalent
  • Acyloin
  • Benzoin
  • N-heterocyclic carbene
  • Organocatalysis
  • Reductive coupling
  • Umpolung
  • α-Hydroxy ketone

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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