Cooperative Catalysis with Iron and a Chiral Bronsted Acid for Asymmetric Reductive Amination of Ketones

被引：77

作者：

Zhou, Shaolin ^{[1
,2
]}

Fleischer, Steffen ^{[1
]}

Jiao, Haijun ^{[1
]}

Junge, Kathrin ^{[1
]}

Beller, Matthias ^{[1
]}

机构：

[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[2] Cent China Normal Univ, CCNU OttawaU Joint Res Ctr, State Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, Wuhan 430079, Hubei, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 16期

基金：

美国国家科学基金会;

关键词：

amines; Bronsted acids; catalysis; iron; reductive amination; ENANTIOSELECTIVE HYDROGENATION; TRANSITION-METAL; ALKYLATION; ALDEHYDES;

D O I：

10.1002/adsc.201400328

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The direct asymmetric reductive amination (DARA) of ketones with anilines is described by combining a chiral Bronsted acid (TRIP) and the non-chiral Knolker iron complex as the catalyst system. In situ-formed imines are reduced with molecular hydrogen to give chiral amines in high yields (90%) and enantioselectivities of up to 99% ee.

引用

页码：3451 / 3455

页数：5

共 41 条

[1]

[Anonymous], INT J ORG CHEM

[2]

[Anonymous], 2007, Handbook of homogeneous hydrogenation

[3]

Blaser HU, 1999, SYNLETT, P867

[4] A facile one-pot synthesis of chiral β-amino esters [J].

Bunlaksananusorn, T ;

Rampf, F .

SYNLETT, 2005, (17) :2682-2684

[5] ENANTIOSELECTIVE HYDROGENATION OF THE C=N GROUP - A CATALYTIC ASYMMETRIC REDUCTIVE AMINATION PROCEDURE [J].

BURK, MJ ;

FEASTER, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (15) :6266-6267

[6] CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND [J].

BURK, MJ ;

MARTINEZ, JP ;

FEASTER, JE ;

COSFORD, N .

TETRAHEDRON, 1994, 50 (15) :4399-4428

[7] Efficient preparation of an N-aryl β-amino acid via asymmetric hydrogenation and direct asymmetric reductive amination en route to Ezetimibe [J].

Busscher, Guuske F. ;

Lefort, Laurent ;

Cremers, Jozef G. O. ;

Mottinelli, Marco ;

Wiertz, Roel W. ;

de Lange, Ben ;

Okamura, Yutaka ;

Yusa, Yukinori ;

Matsumura, Kazuhiko ;

Shimizu, Hideo ;

de Vries, Johannes G. ;

de Vries, Andre H. M. .

TETRAHEDRON-ASYMMETRY, 2010, 21 (13-14) :1709-1714

[8] One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes [J].

Byun, Eunyoung ;

Hong, Bomi ;

De Castro, Kathlia A. ;

Lim, Minkyung ;

Rhee, Hakjune .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9815-9817

[9] Direct Catalytic Asymmetric Reductive Amination of Simple Aromatic Ketones [J].

Chang, Mingxin ;

Liu, Shaodong ;

Huang, Kexuan ;

Zhang, Xumu .

ORGANIC LETTERS, 2013, 15 (17) :4354-4357

[10] 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

← 1 2 3 4 5 →