Diastereoselective three-component Mannich reaction catalyzed by silica-supported ferric hydrogensulfate

被引：20

作者：

Eshghi, Hossein ^{[1
]}

Rahimizadeh, Mohammad ^{[1
]}

Hosseini, Mohsen ^{[1
]}

Javadian-Saraf, Aida ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Sch Sci, Dept Chem, Mashhad 917751436, Iran

来源：

MONATSHEFTE FUR CHEMIE | 2013年 / 144卷 / 02期

关键词：

Three-component; Diastereoselective anti-Mannich reaction; Silica-supported ferric hydrogensulfate; Iron heterogeneous catalysis; 3 COMPONENT SYNTHESIS; BETA-AMINO KETONES; ONE-POT; ANTI-MANNICH; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; AROMATIC-ALDEHYDES; IONIC LIQUID; ACID; EFFICIENT;

D O I：

10.1007/s00706-012-0800-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly anti-diastereoselective three-component Mannich reaction of aromatic amines and aromatic aldehydes with cyclohexanone in the presence of silica-supported ferric hydrogensulfate has been developed. The best selectivity was obtained where there were electron-donating groups on both aldehyde and amine. Selectivity decreases when electron-withdrawing groups are present on the aldehyde; in these cases selectivity is improved if an electron-donating group is present on the amine.

引用

页码：197 / 203

页数：7

共 60 条

[31] Silica-Supported Boric Acid with Ionic Liquid: A Novel Recyclable Catalytic System for One-Pot Three-Component Mannich Reaction [J].

Kumar, Vishal ;

Sharma, Upendra ;

Verma, Praveen Kumar ;

Kumar, Neeraj ;

Singh, Bikram .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2011, 59 (05) :639-645

[32] Direct Mannich reaction mediated by Fe(Cp)2PF6 under solvent-free conditions [J].

Kureshy, Rukhsana I. ;

Agrawal, Santosh ;

Saravanan, S. ;

Khan, Noor-ul H. ;

Shah, Arpan K. ;

Abdi, Sayed H. R. ;

Bajaj, Hari C. ;

Suresh, E. .

TETRAHEDRON LETTERS, 2010, 51 (03) :489-494

[33] 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

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

List, B .

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

[35] 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

[36] Mannich reactions catalyzed by perchloric acid in Triton X10 aqueous micelles [J].

Lu, Guo-ping ;

Cai, Chun .

CATALYSIS COMMUNICATIONS, 2010, 11 (08) :745-748

[37] Mannich-type reactions of aldehydes, amines, and ketones in a colloidal dispersion system created by a Bronsted acid-surfactant-combined catalyst in water [J].

Manabe, K ;

Kobayashi, S .

ORGANIC LETTERS, 1999, 1 (12) :1965-1967

[38] Highly Active Organocatalysts for Asymmetric anti-Mannich Reactions [J].

Martin-Rapun, Rafael ;

Fan, Xinyuan ;

Sayalero, Sonia ;

Bahramnejad, Mahboubeh ;

Cuevas, Felix ;

Pericas, Miquel A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (32) :8780-8783

[39] 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

[40] HIGHLY STEREOSELECTIVE SYNTHESIS OF β-AMINO KETONES VIA A MANNICH REACTION CATALYZED BY CELLULOSE SULFURIC ACID AS A BIODEGRADABLE, EFFICIENT, AND RECYCLABLE HETEROGENEOUS CATALYST [J].

Nemati, Firouzeh ;

Fakhaei, Amir Soheyl ;

Amoozadeh, Ali ;

Hayeniaz, Yaser Saeidi .

SYNTHETIC COMMUNICATIONS, 2011, 41 (24) :3695-3702

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