Mechanistic Understanding of Proline Analogs and Related Protic Lewis Bases (n - π*)

Alan Armstrong*, Paul Dingwall

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter


Proline has played a pivotal role in the development of the field of organocatalysis and is regarded by many as the archetypal organocatalyst. Indeed, proline has been known as a catalyst of the intramolecular aldol reaction since the 1970s, in what was originally thought to be a solitary example of novel reactivity. A mechanistic understanding of proline catalysis has the potential to allow the design of improved catalysts and reaction conditions. The chapter discusses the mechanism of the proline-catalyzed aldol reaction, including the Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction, the Houk-List model, the Seebach-Eschenmoser Model. It also discusses the proline-catalyzed α-amination and α-aminoxylation reactions. Proline-mediated conjugate addition reactions, in which the nucleophile is the carbonyl α-carbon, were first reported in 2001. Then, the chapter explains the modified proline derivatives including proline tetrazole, and the Houk-List model and proline analogs.

Original languageEnglish
Title of host publicationLewis Base Catalysis in Organic Synthesis
PublisherWiley-VCH Verlag
Number of pages46
ISBN (Electronic)9783527675142
ISBN (Print)9783527336180
Publication statusPublished - 17 Aug 2016


  • Additives
  • Aldol
  • DFT
  • Enamine
  • Hajos-Parrish-Eder-Sauer-Wiechert (HPESW) reaction
  • Houk-List model
  • Iminium ion
  • Mechanism
  • Prolinate catalyst
  • Proline catalyst
  • Proline derivative catalysts
  • Reaction kinetics
  • Seebach-Eschenmoser model
  • α-amination
  • α-aminoxylation

ASJC Scopus subject areas

  • Chemistry(all)

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