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Issue 11, 2009
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Bond formations by intermolecular and intramolecular trappings of acylketenes and their applications in natural product synthesis

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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.

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

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Article information


Submitted
25 Jun 2009
First published
02 Sep 2009

Chem. Soc. Rev., 2009,38, 3022-3034
Article type
Tutorial Review

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

K. P. Reber, S. D. Tilley and E. J. Sorensen, Chem. Soc. Rev., 2009, 38, 3022
DOI: 10.1039/B912599J

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