Rhodium-catalyzed [2+2+2] cycloaddition reactions of terminal alkynes with N-sulfonyl ketimines

被引：5

作者：

Zhang, Wei ^{[1
]}

Zhang, Qian-Ru ^{[1
]}

Dong, Lin ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, West China Sch Pharm, Chengdu 610041, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 03期

关键词：

1,2-Dihydropyridines; Rhodium; Terminal alkynes; 2+2+2] cycloaddition; N-Sulfonyl ketimines; STEREOSELECTIVE-SYNTHESIS; AZA-NICKELACYCLE; IMINES; PYRIDINES; 1,2-DIHYDROPYRIDINES; CYCLIZATION; CHEMISTRY;

D O I：

10.1016/j.tetlet.2014.11.122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple approach for the direct synthesis of 1,2-dihydropyridines was developed involving a one-step rhodium-catalyzed [2+2+2] cycloaddition between N-sulfonyl ketimines and two terminal alkynes. Mechanistic studies suggested a stepwise reaction of an imine and alkyne with rhodium(III), followed by the insertion of a second alkyne. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：546 / 548

页数：3

共 35 条

[1] Nickel-Catalyzed, Directing-Group-Assisted [2+2+2] Cycloaddition of Imine and Alkynes [J].

Adak, Laksmikanta ;

Chan, Wei Chuen ;

Yoshikai, Naohiko .

CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) :359-362

[2] Highly Enantioselective Rhodium-Catalyzed [2+2+2] Cycloaddition of Diynes to Sulfonimines [J].

Amatore, Muriel ;

Leboeuf, David ;

Malacria, Max ;

Gandon, Vincent ;

Aubert, Corinne .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (12) :4576-4579

[3] Total synthesis of (+)-lepadin B: Stereoselective synthesis of nonracemic polysubstituted hydroquinolines using an RC-ROM process [J].

Barbe, Guillaume ;

Charette, Andre B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (42) :13873-13875

[4] Copper-catalyzed coupling of pyridines and quinolines with alkynes: A one-step, asymmetric route to functionalized heterocycles [J].

Black, Daniel A. ;

Beveridge, Ramsay E. ;

Arndtsen, Bruce A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1906-1910

[5] Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselective Addition to N-Activated Pyridines [J].

Bull, James A. ;

Mousseau, James J. ;

Pelletier, Guillaume ;

Charette, Andre B. .

CHEMICAL REVIEWS, 2012, 112 (05) :2642-2713

[6] Aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines with HIO3 and I2O5 in water [J].

Chai, Lingzhi ;

Zhao, Yankai ;

Sheng, Qiuju ;

Liu, Zhong-Quan .

TETRAHEDRON LETTERS, 2006, 47 (52) :9283-9285

[7] Practical and highly regio- and stereoselective synthesis of 2-substituted dihydropyridines and piperidines: Application to the synthesis of (-)-coniine [J].

Charette, AB ;

Grenon, M ;

Lemire, A ;

Pourashraf, M ;

Martel, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (47) :11829-11830

[8] Beyond Reppe: Building Substituted Arenes by [2+2+2] Cycloadditions of Alkynes [J].

Galan, Brandon R. ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) :2830-2834

[9] Recent progress in cobalt-mediated [2+2+2] cycloaddition reactions [J].

Gandon, Vincent ;

Aubert, Corinne ;

Malacria, Max .

CHEMICAL COMMUNICATIONS, 2006, (21) :2209-2217

[10] Nickel-Catalyzed Synthesis of N-Aryl-1,2-dihydropyridines by [2+2+2] Cycloaddition of Imines with Alkynes through T-Shaped 14-Electron Aza-Nickelacycle Key Intermediates [J].

Hoshimoto, Yoichi ;

Ohata, Tomoya ;

Ohashi, Masato ;

Ogoshi, Sensuke .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (14) :4105-4110

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