Gold-Catalyzed Hydroalkoxylation/Povarov Reaction Cascade of Alkynols with N-Aryl Imines: Synthesis of Tetrahydroquinolines

被引：23

作者：

He, Ciwang ^{[1
]}

Cai, Ju ^{[1
]}

Zheng, Yang ^{[1
]}

Pei, Chao ^{[1
]}

Qiu, Lihua ^{[1
]}

Xu, Xinfang ^{[1
,2
,3
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Guangdong, Peoples R China

[3] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

来源：

ACS OMEGA | 2019年 / 4卷 / 13期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; POVAROV REACTION; COOPERATIVE CATALYSIS; ALCOHOLS; DERIVATIVES; EFFICIENT; STRATEGY; ACCESS; ACIDS;

D O I：

10.1021/acsomega.9b02693

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A one-pot gold-catalyzed hydroalkoxylation/Povarov reaction cascade of alkynols with N-aryl imines or in situ generated iminium has been developed. The protocol provides a facile access to a series of fused tricyclic tetrahydroquinolines with a broad substrate scope using readily available materials under mild conditions. The unique mechanistic feature is the dual function of the gold catalyst, which first catalyzed the intramolecular hydroalkoxylation of alkynols, and upon the formation of dihydrofuran species, promoted the following Povarov reaction with high stereo-selectivity.

引用

页码：15754 / 15763

页数：10

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