Enantioenriched Naphthoquinone Mannich Bases by Organocatalyzed Nucleophilic Additions to in situ Formed Imines

被引：10

作者：

Ayaz, Muhammad ^{[1
]}

Westermann, Bernhard ^{[1
,2
]}

机构：

[1] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Germany

[2] Univ Halle Wittenberg, Inst Organ Chem, D-06120 Halle, Germany

来源：

SYNLETT | 2010年 / 10期

关键词：

organocatalysis; enantioselective Mannich reaction; 1,4-addition; alpha-amidosulfone; naphthoquinone; ENANTIOSELECTIVE MICHAEL ADDITION; DYNAMIC KINETIC RESOLUTION; CELL-GROWTH; KETONES;

D O I：

10.1055/s-0029-1219946

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalytic nucleophilic addition of 2-hydroxyl-naphthaquinone to imines is reported. This new route can be used to produce enantioenriched Mannich bases with excellent yields and moderate enantioselectivities.

引用

页码：1489 / 1492

页数：4

共 37 条

[1] Chiral Bronsted acid catalyzed enantioselective hydrophosphonylation of imines:: Asymmetric synthesis of α-amino phosphonates [J].

Akiyama, T ;

Morita, H ;

Itoh, J ;

Fuchibe, K .

ORGANIC LETTERS, 2005, 7 (13) :2583-2585

[2] Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].

Austin, JF ;

Kim, SG ;

Sinz, CJ ;

Xiao, WJ ;

MacMillan, DWC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487

[3] Synthesis and in vitro activities of ferrocenic aminohydroxynaphthoquinones against Toxoplasma gondii and Plasmodium falciparum [J].

Baramee, A ;

Coppin, A ;

Mortuaire, M ;

Pelinski, L ;

Tomavo, S ;

Brocard, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1294-1302

[4] Highly efficient dynamic kinetic resolution of azlactones by urea-based bifunctional organocatalysts [J].

Berkessel, A ;

Cleemann, F ;

Mukherjee, S ;

Müller, TN ;

Lex, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) :807-811

[5] Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones [J].

Berkessel, Albrecht ;

Mukherjee, Santanu ;

Mueller, Thomas N. ;

Cleemann, Felix ;

Roland, Katrin ;

Brandenburg, Marc ;

Neudoerfl, Joerg-M. ;

Lex, Johann .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (23) :4319-4330

[6] Organocatalytic asymmetric α-bromination of aldehydes and ketones [J].

Bertelsen, S ;

Halland, N ;

Bachmann, S ;

Marigo, M ;

Braunton, A ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2005, (38) :4821-4823

[7] Organocatalysis-after the gold rush [J].

Bertelsen, Soren ;

Jorgensen, Karl Anker .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189

[8] Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives bearing anti-trypanosomal and anti-leishmanial activity [J].

Bolognesi, Maria Laura ;

Lizzi, Federica ;

Perozzo, Remo ;

Brun, Reto ;

Cavalli, Andrea .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) :2272-2276

[9] Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].

Brochu, MP ;

Brown, SP ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109

[10] A highly enantioselective catalytic desymmetrization of cyclic anhydrides with modified cinchona alkaloids [J].

Chen, YG ;

Tian, SK ;

Deng, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (39) :9542-9543

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