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

作者：Reber Keith P; Tilley S David; Sorensen Erik J^*

来源：Chemical Society Reviews, 2009, 38(11): 3022-3034.

DOI：10.1039/b912599j

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.

• 出版日期2009