Cho Ho-Jun, Kim Ju Hyun
Department of Chemistry (BK21 Four), Research Institute of Natural Science, Gyeongsang National University, Jinju 52828, Korea.
Org Biomol Chem. 2023 Dec 13;21(48):9507-9518. doi: 10.1039/d3ob01619f.
Transition metal-catalyzed dipolar cycloaddition is one of the most efficient and powerful synthetic strategies to produce diverse heterocycles. In particular, for the construction of oxygen-containing heterocycles, which are valuable structural motifs found in pharmaceuticals and natural compounds, transition metal-catalyzed oxa-dipolar cycloaddition using an oxygen-containing dipole has emerged as a promising method. In recent years, the 1,4-O/C dipole synthons 2-alkylidenetrimethylene carbonate and 2-hydroxymethylallyl carbonate have been developed and successfully applied to palladium-catalyzed oxa-[4 + ] dipolar cycloadditions with diverse dipolarophiles. In this review, we summarize recent advances in palladium-catalyzed oxa-[4 + ] dipolar cycloadditions using 1,4-O/C dipoles including asymmetric catalysis and divergent catalysis toward five- to nine-membered O-heterocycles.
过渡金属催化的偶极环加成反应是合成多种杂环化合物最有效且强大的合成策略之一。特别是对于构建含氧化合物的杂环，这些结构基元在药物和天然化合物中很有价值，使用含氧化偶极体的过渡金属催化的氧杂偶极环加成反应已成为一种很有前景的方法。近年来，1,4-O/C偶极体合成子2-亚烷基碳酸三亚甲基酯和2-羟甲基烯丙基碳酸酯已被开发，并成功应用于钯催化的与多种亲偶极体的氧杂-[4 + ]偶极环加成反应。在本综述中，我们总结了使用1,4-O/C偶极体的钯催化氧杂-[4 + ]偶极环加成反应的最新进展，包括对五至九元含氧杂环的不对称催化和发散催化。
