Ring Opening/C-N Cyclization of Activated Aziridines with Carbon Nucleophiles: Highly Diastereo- and Enantioselective Synthesis of Tetrahydroquinolines

被引：59

作者：

Ghorai, Manas K. ^{[1
]}

Nanaji, Y. ^{[1
]}

Yadav, A. K. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 16期

关键词：

DIELS-ALDER REACTION; PD-CATALYZED AMINATION; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; QUINOLINE DERIVATIVES; GALIPEA-OFFICINALIS; FACILE SYNTHESIS; ARYL CHLORIDES; NMDA RECEPTOR; 1,2,3,4-TETRAHYDROQUINOLINES;

D O I：

10.1021/ol2016077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple strategy for the synthesis of substituted tetrahydroquinolines through regio- and stereoselective ring opening of N-tosyl aziridines with carbon nucleophiles generated from 2-(bromoaryl)acetonitriles followed by palladium-catalyzed intramolecular C-N cyclization Is reported in excellent yields (up to > 99%) and stereoselectivity (ee and de up to > 99%).

引用

页码：4256 / 4259

页数：4

共 88 条

[1] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction [J].

Akiyama, Takahiko ;

Morita, Hisashi ;

Fuchibe, Kohei .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13070-13071

[2] Discovering some novel tetrahydroquinoline derivatives bearing the biologically active sulfonamide moiety as a new class of antitumor agents [J].

Alqasoumi, Saleh I. ;

Al-Taweel, Areej M. ;

Alafeefy, Ahmed M. ;

Ghorab, Mostafa M. ;

Noaman, Eman .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) :1849-1853

[3] Intramolecular arylation reactions of alkenes:: A flexible approach to chromans and tetrahydroquinoline derivatives [J].

Barluenga, J ;

Trincado, M ;

Rubio, E ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3416-3417

[4] Conjugate Addition of Lithium N-Phenyl-N-(α-methylbenzyl)amide: Application to the Asymmetric Synthesis of (R)-(-)-Angustureine [J].

Bentley, Scott A. ;

Davies, Stephen G. ;

Lee, James A. ;

Roberts, Paul M. ;

Thomson, James E. .

ORGANIC LETTERS, 2011, 13 (10) :2544-2547

[5] Ag(I)-Catalyzed Regioselective Ring-Opening of N-Tosylaziridine and N-Tosylazetidine with S-, O-, and N-Nucleophiles and Tethered Dinucleophiles [J].

Bera, Milan ;

Pratihar, Sanjay ;

Roy, Sujit .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1475-1478

[6] Alumina-Supported Cu(II), A Versatile and Recyclable Catalyst for Regioselective Ring Opening of Aziridines and Epoxides and Subsequent Cyclization to Functionalized 1,4-Benzoxazines and 1,4-Benzodioxanes [J].

Bhadra, Sukalyan ;

Adak, Laksmikanta ;

Samanta, Subhas ;

Islam, A. K. M. Maidul ;

Mukherjee, Manabendra ;

Ranu, Brindaban C. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8533-8541

[7] Construction of three contiguous tertiary stereocenters from Aziridines in one step [J].

Blyumin, Evgeniy V. ;

Gallon, Helen J. ;

Yudin, Andrei K. .

ORGANIC LETTERS, 2007, 9 (23) :4677-4680

[8] Novel syntheses of azetidines and azetidinones [J].

Brandi, Alberto ;

Cicchi, Stefano ;

Cordero, Franca M. .

CHEMICAL REVIEWS, 2008, 108 (09) :3988-4035

[9] 6-nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-SNAr reaction [J].

Bunce, Richard A. ;

Nago, Takahiro .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (04) :1155-1160

[10] Intramolecular π-π Stacking Interactions in 2-Substituted N,N-Dibenzylaziridinium Ions and Their Regioselectivity in Nucleophilic Ring-Opening Reactions [J].

Catak, Saron ;

D'hooghe, Matthias ;

De Kimpe, Norbert ;

Waroquier, Michel ;

Van Speybroeck, Veronique .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) :885-896

← 1 2 3 4 5 6 7 8 9 →