Mn-Catalyzed Three-Component Reactions of Imines/Nitriles, Grignard Reagents, and Tetrahydrofuran: An Expedient Access to 1,5-Amino/Keto Alcohols

被引：89

作者：

He, Ruoyu ^{[1
]}

Jin, Xiqing ^{[1
]}

Chen, Hui ^{[2
]}

Huang, Zhi-Tang ^{[1
]}

Zheng, Qi-Yu ^{[1
]}

Wang, Congyang ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Inst Chem, CAS Key Lab Photochem, Beijing 100190, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 18期

基金：

中国国家自然科学基金;

关键词：

C BOND FORMATION; H BONDS; ETHERS; INSERTION; ARYL; FUNCTIONALIZATION; ACTIVATION; ALKALOIDS; CHEMISTRY; ALDEHYDES;

D O I：

10.1021/ja503520t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An expedient Mn-catalyzed three-component synthesis of 1,5-amino/keto alcohols from Grignard reagents, imines/nitriles, and tetrahydrofuran (THF) is described, which deviates from the classic Grignard addition to imines/nitriles in THF solvent. THF is split and "sewn" in an unprecedented manner in the reaction, leading to the formation of two geminal C-C bonds via C-H and C-O cleavage. Mechanistic experiments and DFT calculations reveal radical and organo-Mn intermediates in the catalytic cycle and the alpha-arylative ringopening of THF as the key reaction step.

引用

页码：6558 / 6561

页数：4

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