Palladium-Catalyzed Tandem Cycloisomerization/Cross-Coupling of Carbonyl- and Imine-Tethered Alkylidenecyclopropanes

被引：11

作者：

Verdugo, Felipe ^{[1
,2
]}

Rodino, Ricardo ^{[1
,2
]}

Calvelo, Martin ^{[1
,2
]}

Mascarenas, Jose Luis ^{[1
,2
]}

Lopez, Fernando ^{[1
,2
,3
]}

机构：

[1] Univ Santiago de Compostela, Ctr Singular Invest Quim Biol & Mat Mol CIQUS, Santiago De Compostela, Spain

[2] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela, Spain

[3] CSIC, Mision Biol Galicia MBG, Pontevedra 36680, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 24期

关键词：

Alkylidenecyclopropanes; Boronic Acids; Cycloisomerization; Palladium Catalysis; Tandem Reaction; 3+2 INTRAMOLECULAR CYCLOADDITION; ETHYL CYCLOPROPYLIDENEACETATE; ALKYNES; ALK-5-YNYLIDENECYCLOPROPANES; ALKENYLIDENECYCLOPROPANES; ALKYNYLIDENECYCLOPROPANES; CARBOCYCLIZATION; TRANSFORMATIONS; TRANSMETALATION; COCYCLIZATION;

D O I：

10.1002/anie.202202295

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Pd-0 catalysts featuring phosphorus-based monodentate ligands can detour the reactivity of carbonyl-tethered alkylidenecyclopropanes (ACPs) from standard (3+2) cycloadditions towards tandem cycloisomerization/cross-coupling processes. This new reactivity lies on the formation of key pi-allyl oxapalladacyclic intermediates, which are subsequently trapped with external nucleophilic partners, instead of undergoing canonical C-O reductive eliminations. Importantly, the use of imine-tethered ACP's is also feasible. Therefore, the method provides a straightforward and stereoselective entry to a wide variety of highly functionalized cyclic alcohols and amines.

引用

页数：7

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