Gold-Catalyzed Amine Cascade Addition to Diyne-Ene: Enantioselective Synthesis of 1,2-Dihydropyridines

被引：5

作者：

Wei, Jingwen ^{[1
]}

Xing, Yangyang ^{[2
]}

Ye, Xiaohan ^{[1
]}

Nguyen, Bao ^{[1
]}

Wojtas, Lukasz ^{[1
]}

Hong, Xin ^{[2
]}

Shi, Xiaodong ^{[1
]}

机构：

[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA

[2] Zhejiang Univ, Ctr Chem Frontier Technol, Dept Chem, Hangzhou 310027, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2023年 / 62卷 / 31期

基金：

国家重点研发计划; 中国国家自然科学基金;

关键词：

Dihydropyridine; Diyne-Ene; Enantioselective; Gold Catalysis; TERMINAL ALKYNES; PIPERIDINE; CYCLOISOMERIZATION; PYRROLIDINE; ACTIVATION; ALKALOIDS; PYRIDINES; DEAROMATIZATION; COMPLEXES; ARYLATION;

D O I：

10.1002/anie.202305409

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

With the well-documented chemical and biological applications, piperidine and pyridine are among the most important N-heterocycles, and a new synthetic strategy, especially one with an alternative bond-forming design, is of general interest. Using the gold-catalyzed intermolecular condensation of amine and diyne-ene, we report herein the first example of enantioselective 1,2-dihydropyridine synthesis through a formal [3+2+1] fashion (up to 95 % yield, up to 99 % e.e.).

引用

页数：6

共 50 条

[41] Gold-Catalyzed Reaction of Propargyl Esters and Alkynylsilanes: Synthesis of Vinylallene Derivatives through a Twofold 1,2-Rearrangement
Bernardo, Olaya
Gonzalez-Pelayo, Silvia
Fernandez, Israel
Lopez, Luis A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (48) : 25258 - 25262
[42] Silver(I)-Catalyzed Tandem Reaction of Enynones and 4-Alkenyl Isoxazoles: Synthesis of 2-(Furan-2-yl)-1,2-dihydropyridines
Peng, Haiyun
Zhang, Yangyi
Deng, Guisheng
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7038 - 7045
[43] Gold-Catalyzed Cascade Reactions of Furan-ynes with External Nucleophiles Consisting of a 1,2-Rearrangement: Straightforward Synthesis of Multi-Substituted Benzo[b]furans
Sun, Ning
Xie, Xin
Liu, Yuanhong
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) : 7514 - 7519
[44] Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds through a Redox/[2+2+1] Cycloaddition Cascade of Nitroalkyne Substrates
Jadhav, Appaso Mahadev
Bhunia, Sabyasachi
Liao, Hsin-Yi
Liu, Rai-Shung
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) : 1769 - 1771
[45] Gold-Catalyzed Synthesis of 1-(Indo1-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migration
Suarez, Anisley
Suarez-Pantiga, Samuel
Nieto-Faza, Olalla
Sanz, Roberto
ORGANIC LETTERS, 2017, 19 (19) : 5074 - 5077
[46] Gold-Catalyzed Oxidative Reactions of Propargylic Carbonates Involving 1,2-Carbonate Migration: Stereoselective Synthesis of Functionalized Alkenes
Sun, Ning
Chen, Ming
Liu, Yuanhong
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09): : 4055 - 4067
[47] Gold-Catalyzed One-Pot Cascade Construction of Highly Functionalized Pyrrolo[1,2-a]quinolin-1(2H)-ones
Zhou, Yu
Feng, Enguang
Liu, Guannan
Ye, Deju
Li, Jian
Jiang, Hualiang
Liu, Hong
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19): : 7344 - 7348
[48] A facile diversity-oriented synthesis of imidazo[1,2-a]pyrazinones via gold-catalyzed regioselective heteroannulation of propynylaminopyrazinones
Vachhani, Dipak D.
Modha, Sachin G.
Sharma, Abhishek
Van der Eycken, Erik V.
TETRAHEDRON, 2013, 69 (01) : 359 - 365
[49] Gold-catalyzed intramolecular cyclization/condensation sequence: synthesis of 1,2-dihydro[c][2,7]naphthyridines
Goutham, Kommuru
Kadiyala, Veerabhushanam
Sridhar, Balasubramanian
Karunakar, Galla V.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (37) : 7813 - 7818
[50] Synthesis of Pyrrolo[1,2-b]isoquinolines via Gold(I)-Catalyzed Cyclization/Enyne Cycloisomerization/1,2-Migration Cascade
Song, Liangliang
Tian, Guilong
Van Meervelt, Luc
Van der Eycken, Erik V.
ORGANIC LETTERS, 2020, 22 (16) : 6537 - 6542

← 1 2 3 4 5 →