Mi Chun-Yu, Zhai Jia-Yuan, Zhang Xiao-Ming
State Key Laboratory of Natural Product Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
Beilstein J Org Chem. 2025 May 22;21:999-1009. doi: 10.3762/bjoc.21.81. eCollection 2025.
Enamides are distinctive amphiphilic synthons that can be strategically incorporated into cyclization reactions. The iminium species generated from enamides via nucleophilic addition or substitution are capable of engaging in further electrophilic additions or isomerization processes. Exploiting the multiple reactivities of enamides facilitates the development of diverse cyclization modes that provide entries to various -heterocycles, some of which serve as key structural motifs in natural alkaloids. This review highlights recent advancements in enamide-based cyclization reactions, including enamide-alkyne cycloisomerization, [3 + 2] annulation, and polycyclization, with a particular emphasis on their pivotal role as a strategy in the total synthesis of natural products.
烯酰胺是独特的两亲性合成子，可策略性地用于环化反应。通过亲核加成或取代从烯酰胺生成的亚胺鎓物种能够进行进一步的亲电加成或异构化过程。利用烯酰胺的多种反应性有助于开发各种环化模式，从而构建各种杂环，其中一些是天然生物碱的关键结构单元。本综述重点介绍了基于烯酰胺的环化反应的最新进展，包括烯酰胺-炔环异构化、[3+2]环化和多环化，特别强调了它们在天然产物全合成中作为一种策略的关键作用。
