Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole

被引：12

作者：

Chen, Guzhou ^{[1
]}

Liu, Peng-Yu ^{[2
]}

Zou, Huanhuan ^{[1
]}

Hu, Jiadong ^{[3
]}

Fang, Xiaowu ^{[1
]}

Xu, Dongyang ^{[1
]}

He, Yu-Peng ^{[2
]}

Wei, Hongbo ^{[1
]}

Xie, Weiqing ^{[1
,4
]}

机构：

[1] Northwest A&F Univ, Coll Chem & Pharm, Shaanxi Key Lab Nat Prod & Chem Biol, Yangling 712100, Shaanxi, Peoples R China

[2] Liaoning Shihua Univ, Key Lab Petrochem Catalyt Sci & Technol, Fushun 113001, Peoples R China

[3] Yangling Vocat & Tech Coll, Xianyang, Shaanxi, Peoples R China

[4] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 06期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/acs.orglett.1c00411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose herein a Au(I)-catalyzed domino cyclization of 1,6-diynes incorporated with indole. This protocol enabled the diastereoselective buildup of indole-fused azabicyclo[3.3.1]nonanes from linear precursors. Density functional theory calculations showed that the reaction proceeded via an unprecedented cascade dearomatization/rearomatization/dearomatization process. Independent gradient model analysis revealed that a noncovalent attractive interaction between the distal alkyne and the Au/proximal complex was responsible for the chemoselectivity of the first spirocyclization step.

引用

页码：2279 / 2284

页数：6

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