Scope of the organocatalysed asymmetric reductive amination of ketones with trichlorosilane

被引：40

作者：

Gautier, Francois-Moana ^{[1
]}

Jones, Simon ^{[1
]}

Li, Xianfu ^{[1
]}

Martin, Stephen J. ^{[2
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Aesica Pharmaceut Ltd, Cramlington NE23 3JL, Northd, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 22期

关键词：

N-ARYL IMINES; ENANTIOSELECTIVE HYDROGENATION; ORGANOLITHIUM REAGENTS; AMINES; KETIMINES; LIGANDS; ALKYLATION; COMPLEXES; ALDEHYDES; CATALYSTS;

D O I：

10.1039/c1ob05965c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly active organocatalyst has been shown to affect the asymmetric reductive amination of ketones producing both aromatic and aliphatic amines. At 1 mol% catalyst loading, a series of structurally diverse chiral amines were quickly and economically prepared with good enantioselectivity and generally useful yield. The efficient synthesis of the calcimimetic (+)-NPS R-568 (67%, 89% ee) demonstrated the synthetic applicability of this methodology.

引用

页码：7860 / 7868

页数：9

共 49 条

[21] Highly enantioselective hydrogen-transfer reductive amination: Catalytic asymmetric synthesis of primary amines [J].

Kadyrov, R ;

Riermeier, TH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) :5472-5474

[22] The first highly enantioselective homogeneously catalyzed asymmetric reductive amination:: Synthesis of α-N-benzylamino acids [J].

Kadyrov, R ;

Riermeier, TH ;

Dingerdissen, U ;

Tararov, V ;

Börner, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4067-4070

[23] Synthesis and biological activity of allosteric modulators of GABAB receptors, Part 1.: N-(phenylpropyl)-1-arylethylamines [J].

Kerr, David I. B. ;

Ong, Jennifer ;

Perkins, Michael V. ;

Prager, Rolf H. ;

Puspawati, Ni Made .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2006, 59 (07) :445-456

[24] Single Nucleotide-Catalyzed Biomimetic Reductive Amination [J].

Kumar, Atul ;

Sharma, Siddharth ;

Maurya, Ram Awatar .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (13) :2227-2232

[25] Asymmetric hydrogenation of cyclic imines with an ionic Cp*Rh(III) catalyst [J].

Li, Chaoqun ;

Xiao, Jianliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) :13208-13209

[26] Chiral Counteranion-Aided Asymmetric Hydrogenation of Acyclic Imines [J].

Li, Chaoqun ;

Wang, Chao ;

Villa-Marcos, Barbara ;

Xiao, Jianliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14450-+

[27] Metal-Bronsted Acid Cooperative Catalysis for Asymmetric Reductive Amination [J].

Li, Chaoqun ;

Villa-Marcos, Barbara ;

Xiao, Jianliang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6967-+

[28] A vaulted biaryl phosphoric acid-catalyzed reduction of α-imino esters:: The highly enantioselective preparation of α-amino esters [J].

Li, Guilong ;

Liang, Yuxue ;

Antilla, Jon C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5830-+

[29] Organocatalysis with a fluorous tag: Asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides [J].

Malkov, Andrei V. ;

Figlus, Marek ;

Stoncius, Sigitas ;

Kocovsky, Pavel .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1315-1325

[30] Enantioselective synthesis of 1,2-diarylaziridines by the organocatalytic reductive amination of α-chloroketones [J].

Malkov, Andrei V. ;

Stoncius, Sigitas ;

Kocovsky, Pavel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (20) :3722-3724

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