Enantioselective Synthesis of 2-Azanorbornanes: Chiral Trisimidazoline-Catalyzed Desymmetrizing Transannular Bromoaminocyclization

被引：0

作者：

Zhu, Wan-Li ^{[1
]}

He, Hao ^{[1
]}

Huang, Yong-Shuang ^{[1
]}

Wang, Ya-Ting ^{[1
]}

Li, You-Gui ^{[2
]}

Wu, Xiang ^{[1
]}

机构：

[1] Hefei Univ Technol, Sch Chem & Chem Engn, Anhui Prov Key Lab Value Added Catalyt Convers & R, Hefei 230009, Peoples R China

[2] Wuyi Univ, Sch Environm & Chem Engn, Jiangmen 529020, Peoples R China

来源：

ORGANIC LETTERS | 2025年 / 27卷 / 13期

关键词：

STEREOSELECTIVE-SYNTHESIS; MICHAEL REACTION; BROMOLACTONIZATION; CONSTRUCTION; DERIVATIVES; FUNCTIONALIZATION; MODULATORS; BACKBONE; GEOMETRY; ACIDS;

D O I：

10.1021/acs.orglett.5c00478

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective desymmetrizing transannular bromoaminocyclization of cyclopentenylamines has been achieved by using C 3-symmetric trisimidazoline catalysis. This protocol could directly provide a range of chiral 2-azanorbornanes in excellent yields (up to 99%) and enantioselectivities (up to 97.5:2.5 enantiomeric ratio). The resulting enantioenriched 2-azanorbornanes are easily converted to synthetically useful building blocks. Further mechanistic investigations show that the presence of three imidazoline groups of the catalyst is crucial to the success of the enantioselective transformation.

引用

页码：3193 / 3198

页数：6

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