High-order dipolar annulations with metal-containing reactive dipoles,Chemical Society Reviews

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High-order dipolar annulations with metal-containing reactive dipoles
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2022-05-06 , DOI: 10.1039/d1cs00897h
Mao-Mao Zhang ₁ , Bao-Le Qu ₁ , Bin Shi ₁ , Wen-Jing Xiao _{1,

2} , Liang-Qiu Lu _{1,

3,

4}

Affiliation

Medium-sized heterocycles are widespread among a spectrum of structurally intriguing and biologically significant natural products and synthetic pharmaceuticals. Metal-catalyzed high-order dipolar annulations resembling reactions of metal-containing reactive dipoles with dipolarophiles constitute a highly efficient and flexible strategy for constructing medium-sized heterocycles. Mechanistically, these annulation reactions usually proceeding through stepwise pathways are different from the classic high-order pericyclic reactions that follow the Woodward–Hoffman rules. More significantly, asymmetric high-order dipolar annulations using chiral organometallic catalysts have been proven successful for constructing chiral medium-sized heterocycles with high enantio- and diastereoselectivity. This review highlights the impressive advances in this area and is focused on the reactivity, scope, mechanisms and applications of high-order dipolar annulation reactions.

中文翻译：

含金属反应偶极子的高阶偶极环化

中等大小的杂环广泛存在于一系列结构有趣且具有生物学意义的天然产物和合成药物中。金属催化的高阶偶极环化类似于含金属的反应偶极子与亲偶极子的反应，构成了构建中等尺寸杂环的高效和灵活的策略。从机理上讲，这些通常通过逐步途径进行的环化反应不同于遵循伍德沃德-霍夫曼规则的经典高阶周环反应。更重要的是，使用手性有机金属催化剂的不对称高阶偶极环化已被证明成功地构建了具有高对映选择性和非对映选择性的手性中等尺寸杂环。

更新日期：2022-05-06

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