Journal
CHEMICAL SOCIETY REVIEWS
Volume 38, Issue 11, Pages 3022-3034Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b912599j
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Funding
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM065483] Funding Source: NIH RePORTER
- NIGMS NIH HHS [R01 GM065483-09, R01 GM065483] Funding Source: Medline
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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 beta-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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