Palladium-Catalyzed Enantio- and Regioselective Ring-Opening Hydrophosphinylation of Methylenecyclopropanes

被引：34

作者：

Zhou, Jian ^{[1
,2
]}

Meng, Ling ^{[1
]}

Lin, Shujuan ^{[3
]}

Cai, Baohua ^{[2
]}

Wang, Jun ^{[1
]}

机构：

[1] Hong Kong Baptist Univ, Dept Chem, Kowloon, Hong Kong, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

[3] Chinese Acad Sci, Fujian Inst Res Struct Matter, State Key Lab Struct Chem, Fuzhou 350002, Fujian, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 26期

基金：

中国国家自然科学基金;

关键词：

C-C Bond Cleavage; C-P Bond Formation; DFT Calculations; Hydrophosphinylation; Phosphine; PHOSPHINE-OXIDE; ASYMMETRIC-SYNTHESIS; 3+2+2 CYCLOADDITIONS; BOND-CLEAVAGE; ALKYLIDENECYCLOPROPANES; ALKYNES; ALKENYLIDENECYCLOPROPANES; CONSTRUCTION; HYDROPHOSPHORYLATION; HYDROAMINATION;

D O I：

10.1002/anie.202303727

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Transition metal-catalyzed hydrofunctionalization of methylenecyclopropanes (MCPs) has presented a considerable challenge due to the difficult manipulation of regioselectivity and complicated reaction patterns. Herein, we report a straightforward Pd-catalyzed ring-opening hydrophosphinylation reaction of MCPs via highly selective C-C bond cleavage. This method allows for rapid and efficient access to a wide range of chiral allylic phosphine oxides in good yields and high enantioselectivities. Additionally, density functional theory (DFT) calculations were performed to elucidate the reaction mechanism and the origin of enantioselectivity.

引用

页数：8

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