Towards a Practical Bronsted Acid Catalyzed and Hantzsch Ester Mediated Asymmetric Reductive Amination of Ketones with Benzylamine

被引：38

作者：

Wakchaure, Vijay N. ^{[1
]}

Nicoletti, Marcello ^{[1
]}

Ratjen, Lars ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany

来源：

SYNLETT | 2010年 / 18期

关键词：

benzylamine; Hantzsch ester; reductive amination; organocatalysis; chiral amines; Bronsted acids; CHIRAL PHOSPHORIC-ACIDS; ALPHA-IMINO ESTERS; TRANSFER HYDROGENATION; ENANTIOSELECTIVE REDUCTION; AROMATIC KETIMINES; ALLYLIC AMINES; TRICHLOROSILANE; ORGANOCATALYSTS; DERIVATIVES; DEPROTECTION;

D O I：

10.1055/s-0030-1259003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the use of benzylamine as the amine component in Hantzsch ester mediated and chiral Bronsted acid catalyzed enantioselective reductive aminations of ketones. The method is noteworthy because the benzyl group is easily removable, and amine product purification is achieved through Hantzsch ester oxidation product removal via basic hydrolysis.

引用

页码：2708 / 2710

页数：3

共 46 条

[1]

Adair G, 2008, ALDRICHIM ACTA, V41, P31

[2] 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

[3] Stronger bronsted acids [J].

Akiyama, Takahiko .

CHEMICAL REVIEWS, 2007, 107 (12) :5744-5758

[4]

Blaser HU, 1999, SYNLETT, P867

[5] Highly enantioselective reductive amination of simple aryl ketones catalyzed by Ir-f-Binaphane in the presence of titanium(IV) isopropoxide and iodine [J].

Chi, YX ;

Zhou, YG ;

Zhang, XM .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4120-4122

[6] Asymmetric organocatalytic reductions mediated by dihydropyridines [J].

Connon, Stephen J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (21) :3407-3417

[7] Chiral phosphoric acids: Powerful organocatalysts for asymmetric addition reactions to imines [J].

Connon, Stephen J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (24) :3909-3912

[8] One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives [J].

Córdova, A .

SYNLETT, 2003, (11) :1651-1654

[9] Diastereoselective synthesis of fluorinated, seven-membered β-amino acid derivatives via ring-closing metathesis [J].

Fustero, S ;

Bartolomé, A ;

Sanz-Cervera, JF ;

Sánchez-Roselló, M ;

Soler, JG ;

de Arellano, CR ;

Fuentes, AS .

ORGANIC LETTERS, 2003, 5 (14) :2523-2526

[10] Novel approach for asymmetric synthesis of fluorinated β-amino sulfones and allylic amines [J].

Fustero, S ;

Soler, JG ;

Bartolomé, A ;

Roselló, MS .

ORGANIC LETTERS, 2003, 5 (15) :2707-2710

← 1 2 3 4 5 →