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Tutorial Review
Chem. Soc. Rev., 2009, 38, 3022 - 3034, DOI: 10.1039/b912599j
Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis
Keith P. Reber, S. David Tilley and Erik J. Sorensen
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
-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.
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