N-Heterocyclic Carbene-Catalyzed Highly Enantioselective Macrolactonization to Access Planar-Chiral Macrocycles

被引：14

作者：

Wang, Jiaming ^{[1
]}

Wang, Meng ^{[2
]}

Wen, Yilu ^{[1
]}

Teng, Peng ^{[3
]}

Li, Chenyang ^{[2
]}

Zhao, Changgui ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Key Lab Radiopharmaceut, Minist Educ, Beijing 100875, Peoples R China

[2] Beijing Normal Univ, Coll Chem, Key Lab Theoret & Computat Photochem, Minist Educ, Beijing 100875, Peoples R China

[3] Zhejiang Univ, Inst Drug Discovery & Design, Coll Pharmaceut Sci, Hangzhou 310058, Zhejiang, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 05期

基金：

中国国家自然科学基金; 北京市自然科学基金;

关键词：

CHEMISTRY;

D O I：

10.1021/acs.orglett.3c04200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-heterocyclic carbene (NHC)-catalyzed atroposelective macrolactonization has been disclosed. This approach affords planar-chiral macrocycles in high yields with excellent enantioselectivities over a broad substrate scope. Controlled experiments suggest that the enantioselectivity might arise from the cation-n interaction between the acyl azolium and the electron-rich moiety in the substrate. This mechanism is supported by density functional theory calculations, which also suggest an important pi-pi interaction in stabilizing the transition state.

引用

页码：1040 / 1045

页数：6

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