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

H. Gotoh, Y. Hayashi

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

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 publicationComprehensive Chirality
PublisherElsevier Ltd
Pages125-156
Number of pages32
Volume6
ISBN (Print)9780080951683
DOIs
Publication statusPublished - 2012 Sep 1
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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