Intermolecular Diels-Alder Reactions

K. Ishihara, A. Sakakura

Research output: Chapter in Book/Report/Conference proceedingChapter

10 Citations (Scopus)

Abstract

The Diels-Alder reaction is one of the most powerful carbon-carbon bond-forming reactions and is a versatile tool for the synthesis of many bioactive natural products. Since it was first shown that the Diels-Alder reaction could be effectively promoted by Lewis acids, stereoselective versions have been extensively investigated. This chapter focuses on representative achievements in this field after publication of the first edition of Comprehensive of Organic Synthesis in 1991. The authors summarize chiral Lewis acid catalysis, including chiral boron(III), copper(II), and other metal complexes, for use in diastereo- and enantioselective Diels-Alder reactions. Next, recent significant advances in asymmetric organocatalysis, including organoammonium catalysis and hydrogen-bonding catalysis, are described. Examples of natural product syntheses based on the asymmetric Diels-Alder reaction using Lewis acid catalysts or organocatalysts are also described. Finally, representative studies on the biomimetic synthesis of natural compounds using intermolecular Diels-Alder reactions are shown.

Original languageEnglish
Title of host publicationComprehensive Organic Synthesis
Subtitle of host publicationSecond Edition
PublisherElsevier Ltd
Pages351-408
Number of pages58
Volume5
ISBN (Print)9780080977430
DOIs
Publication statusPublished - Feb 1 2014

Keywords

  • Asymmetric catalysis
  • Biomimetic synthesis
  • Cycloaddition
  • Diastereoselectivity
  • Diels-Alder reaction
  • Dienes
  • Dienophiles
  • Enantioselectivity
  • Lewis acid catalysts
  • Organocatalysts

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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  • Cite this

    Ishihara, K., & Sakakura, A. (2014). Intermolecular Diels-Alder Reactions. In Comprehensive Organic Synthesis: Second Edition (Vol. 5, pp. 351-408). Elsevier Ltd. https://doi.org/10.1016/B978-0-08-097742-3.00509-7