Formal [2σ+2σ]-Cycloaddition of Aziridines with Bicyclo[1.1.0]butanes: Access to Enantiopure 2-Azabicyclo[3.1.1]heptane Derivatives

被引：37

作者：

Dutta, Shubham ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Muck-Lichtenfeld, Christian ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Organ Chem Inst, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2024年 / 146卷 / 39期

关键词：

2-PI+2-SIGMA CYCLOADDITIONS;

D O I：

10.1021/jacs.4c11296

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Saturated nitrogen heterocycles are among the most significant structural components in small-molecule pharmaceuticals. Herein, a protocol for the construction of enantiopure 2-azabicyclo[3.1.1]heptane derivatives by a stereospecific intermolecular formal cycloaddition of aziridines with bicyclo[1.1.0]butanes is described. The reaction is run by using B(C6F5)(3) as a catalytic additive to give access to a library of enantiopure 2-azabicyclo[3.1.1]heptane derivatives (37 examples) under mild and operationally simple conditions. Successful scale-up reactions, mechanistic experiments, density functional theory (DFT) calculations and synthetic applications are presented.

引用

页码：27204 / 27212

页数：9

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