Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis

Keith P. Reber, S. David Tilley, Erik J. Sorensen

Research output: Contribution to journalArticle

72 Scopus citations

Abstract

The reactive intermediates known as acylketenes exhibit a rich chemistry and have been extensively utilized for many types of inter- and intramolecular bond-forming reactions within the field of organic synthesis. Characteristic reactions of acylketenes include cycloadditions, carbon–carbon bond-forming reactions, and nucleophilic capture with alcohols or amines to give β-keto acid derivatives. In particular, the intramolecular capture of acylketene intermediates with pendant nucleophiles represents a powerful method for forming both medium-sized rings and macrocycles, often in high yield. This tutorial review examines the history, generation, and reactivity of acylketenes with a special focus on their applications in the synthesis of natural products.

Original languageEnglish (US)
Pages (from-to)3022-3034
Number of pages13
JournalChemical Society Reviews
Volume38
Issue number11
DOIs
StatePublished - Oct 22 2009

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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