6.5 C-C Bond Formation: Aldol Reaction with Non-Proline Derivatives

H. Gotoh, Y. Hayashi

Research output: Chapter in Book/Report/Conference proceedingChapter


The aldol reaction is one of the most important carbon-carbon bond-forming reactions in organic synthesis. Since the discovery of intra- and intermolecular aldol reactions catalyzed by proline, organocatalyst-mediated aldol reactions have been developed extensively. Currently, asymmetric organocatalytic aldol reactions can be classified into four major categories, differentiated by their reaction mechanisms: (1) enamine mechanisms; (2) ion-pair mechanisms; (3) chiral enolate mechanisms; and (4) electron acceptor activation by Brønsted acids. In this chapter, the authors describe these four types of aldol reactions; herein, the authors limit their discussion to reactions catalyzed by nonproline derivatives, whereas in the previous chapter, aldol reactions catalyzed by proline and proline derivatives are reviewed.

Original languageEnglish
Title of host publicationSynthetic Methods V - Organocatalysis
PublisherElsevier Ltd
Number of pages32
ISBN (Print)9780080951683
Publication statusPublished - 2012 Sept
Externally publishedYes


  • Direct aldol reactions
  • Enamine
  • Enolate
  • On water reactions
  • Phase-transfer catalyst

ASJC Scopus subject areas

  • Chemistry(all)


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