Enantioselective Dearomative Mizoroki-Heck Reaction of Naphthalenes
Enantioselective Dearomative Mizoroki-Heck Reaction of Naphthalenes
复制标题
萘的对映选择性脱芳香 Mizoroki-Heck 反应
DOI：
10.1021/acscatal.1c05008
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发表时间：
2021-12-23
期刊：
影响因子：
12.9
通讯作者：
Jia, Yi-Xia
中科院分区：
文献类型：
--
作者：
Han, Xiao-Qing;Wang, Lei;Jia, Yi-Xia
钯催化的萘分子内对映选择性 Mizoroki-Heck 反应是通过萘环内 π 键的脱芳香迁移插入，然后消除 δ-氢化物而开发的。该反应依赖于手性磺酰胺膦型Xu-Phos配体的使用，成功抑制了竞争性和不需要的C-H芳基化反应，并有效促进了螺吲哚和螺异吲哚啉-1-酮产物的形成。产品的合成转化提供了一系列独特的杂环化合物，并保留了对映体过量 (ee) 值。
A palladium-catalyzed intramolecular enantioselective Mizoroki-Heck reaction of naphthalenes has been developed via dearomative migratory insertion of an endocyclic pi-bond of naphthalene, followed by delta-hydride elimination. This reaction relies on the use of chiral sulfonamide phosphine type Xu-Phos ligand, which successfully inhibits the competitive and undesired C-H arylation reaction and efficiently promotes the formation of spirooxindole and spiroisoindolin-1-one products. Synthetic transformations of the product afford a series of unique heterocyclic compounds with enantiomeric excess (ee) values retained.