Metal-free Bronsted acid catalyzed transfer hydrogenation - New organocatalytic reduction of quinolines

被引：115

作者：

Rueping, Magnus ^{[1
]}

Theissmann, Thomas ^{[1
]}

Antonchick, Andrey P. ^{[1
]}

机构：

[1] Univ Frankfurt, Inst Organ Chem & Chem Biol, Degussa Endowed Professorship, D-60439 Frankfurt, Germany

来源：

SYNLETT | 2006年 / 07期

关键词：

Bronsted acid; Hantzsch dihydropyridine; transfer hydrogenation; organocatalysis; reduction; 1,2,3,4-tetrahydroquinoline;

D O I：

10.1055/s-2006-939706

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first metal-free Bronsted acid catalyzed hydrogenation of quinolines using Hantzsch dihydropyridine as the hydrogen source has been developed. This, so far unprecedented organocatalytic reduction of heteroaromatic compounds provides a variety of differently substituted 1,2,3,4-tetrahydroquinolines in excellent yields under mild reaction conditions using a remarkably low amount of Bronsted acid catalyst.

引用

收藏

页码：1071 / 1074

页数：4

相关论文

共 49 条

[1] Organocatalytic hydride transfers: A new concept in asymmetric hydrogenations [J].

Adolfsson, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) :3340-3342

[2]

ADOLFSSON H, 2005, ANGEW CHEM, V117, P3404

[3] Enantioselective aza-Diels-Alder reaction catalyzed by a chiral Bronsted acid: Effect of the additive on the enantioselectivity [J].

Akiyama, T ;

Tamura, Y ;

Itoh, J ;

Morita, H ;

Fuchibe, K .

SYNLETT, 2006, (01) :141-143

[4] Enantioselective Mannich-type reaction catalyzed by a chiral bronsted acid derived from TADDOL [J].

Akiyama, T ;

Saitoh, Y ;

Morita, H ;

Fuchibe, K .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (11-13) :1523-1526

[5] 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

[6] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid [J].

Akiyama, T ;

Itoh, J ;

Yokota, K ;

Fuchibe, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) :1566-1568

[7]

Akiyama T., 2004, ANGEW CHEM, V116, P1592, DOI DOI 10.1002/ANGE.200353240

[8]

[Anonymous], 2002, MACROMOL CHEM PHYS

[9] Helquinoline, a new tetrahydroquinoline antibiotic from Janibacter limosus Hel 1 [J].

Asolkar, RN ;

Schröder, D ;

Heckmann, R ;

Lang, S ;

Wagner-Döbler, I ;

Laatsch, H .

JOURNAL OF ANTIBIOTICS, 2004, 57 (01) :17-23

[10] Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].

Bolm, C ;

Rantanen, T ;

Schiffers, I ;

Zani, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763

← 1 2 3 4 5 →