Development of the first Bronsted acid assisted enantioselective Bronsted acid catalyzed direct Mannich reaction

被引：89

作者：

Rueping, Magnus ^{[1
]}

Sugiono, Erli ^{[1
]}

Schoepke, Fenja R. ^{[1
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60438 Frankfurt, Germany

来源：

SYNLETT | 2007年 / 09期

关键词：

Mannich reaction; organocatalysis; Bronsted acid; BINOL-phosphate; cooperative catalysis;

D O I：

10.1055/s-2007-980369

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We here describe the development of the first enantioselective Bronsted acid assisted chiral Bronsted acid catalyzed direct Mannich reaction of acetophenone with various aldimines. The re-action proceeds in the presence of a chiral and an achiral Bronsted acid which simultaneously activate the ketone and aldimine to give the corresponding beta-amino ketones with good enantioselectivities and without the necessity of enolate preformation.

引用

页码：1441 / 1445

页数：5

共 98 条

[51]

Kobayashi S, 2002, CHEM-EUR J, V8, P4185, DOI 10.1002/1521-3765(20020916)8:18<4185::AID-CHEM4185>3.0.CO

[52]

2-6

[53] Catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols [J].

Kobayashi, S ;

Ishitani, H ;

Ueno, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :431-432

[54] The proline-catalyzed direct asymmetric three-component Mannich reaction: Scope, optimization, and application to the highly enantioselective synthesis of 1,2-amino alcohols [J].

List, B ;

Pojarliev, P ;

Biller, WT ;

Martin, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :827-833

[55] The direct catalytic asymmetric three-component Mannich reaction [J].

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9336-9337

[56] Asymmetric Mannich reactions of β-keto esters with acyl imines catalyzed by cinchona alkaloids [J].

Lou, S ;

Taoka, BM ;

Ting, A ;

Schaus, SE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11256-11257

[57] anti-selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing β-amino alcohols [J].

Matsunaga, S ;

Kumagai, N ;

Harada, S ;

Shibasaki, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (16) :4712-4713

[58]

MAYER S, 2006, ANGEW CHEM, V118, P4299

[59] Asymmetric counteranion-directed catalysis [J].

Mayer, Sonja ;

List, Benjamin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (25) :4193-4195

[60] Design of chiral N-triflyl phosphoramide as a strong chiral Bronsted acid and its application to asymmetric Diels-Alder reaction [J].

Nakashima, Daisuke ;

Yamamoto, Hisashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (30) :9626-9627

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