Lewis Base Catalyzed Asymmetric Formal [2+2] Cycloadditions

Andrew D. Smith*, James Douglas, Louis C. Morrill, Edward Richmond

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter

3 Citations (Scopus)

Abstract

Research into the development of new catalytic modes, as exemplified by the rapidly expanding field of organocatalysis, has led to the efficient synthesis of polyfunctionalized molecules with routinely high levels of stereocontrol. This chapter focuses specifically on formal [2+2] cycloadditions catalyzed by Lewis bases, with an exclusive focus on those processes that have been rendered asymmetric. Detailed analysis of reaction design, mechanism, and product utility are made for a range of important four-membered heterocyclic classes, beginning with β-lactams and β-lactones before further expanding to more elaborate architectures, such as aza-β-lactams, β-sultams, and β-sultones. It demonstrates the role and development of Lewis base catalysts in asymmetric ketene homodimerization, the potential utility of such stereodefined polyketide scaffolds, and the emerging field of asymmetric ketene heterodimerization.

Original languageEnglish
Title of host publicationMethods and Applications of Cycloaddition Reactions in Organic Syntheses
PublisherWiley-Blackwell
Pages89-114
Number of pages26
Volume9781118299883
ISBN (Electronic)9781118778173
ISBN (Print)9781118299883
DOIs
Publication statusPublished - 10 Feb 2014

Keywords

  • Asymmetric formal [2+2] cycloadditions
  • Heterodimerization
  • Homodimerization
  • Ketene dimers
  • Ketenes
  • Lewis base
  • β-Lactams
  • β-lactones

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