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 language | English (US) |
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Pages (from-to) | 3022-3034 |
Number of pages | 13 |
Journal | Chemical Society Reviews |
Volume | 38 |
Issue number | 11 |
DOIs | |
State | Published - Oct 22 2009 |
All Science Journal Classification (ASJC) codes
- General Chemistry