Tertiary amines as highly efficient catalysts in the ring-opening reactions of epoxides with amines or thiols in H2O:: expeditious approach to β-amino alcohols and β-aminothioethers

被引：72

作者：

Wu, J

Xia, HG

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

GREEN CHEMISTRY | 2005年 / 7卷 / 10期

关键词：

D O I：

10.1039/b509288d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring-opening of epoxides with various amines or thiols catalyzed by DABCO (1,4-diazabicyclic[2,2,2] octane) or Et3N ( 1 mol%) in water afforded the corresponding products in good to excellent yields under mild reaction conditions.

引用

页码：708 / 710

页数：3

共 24 条

[1] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[2] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[3] Efficient ring-opening reaction of epoxides and aziridines promoted by tributylphosphine in water [J].

Fan, RH ;

Hou, XL .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :726-730

[4]

FAN RH, 2003, THESIS CHINESE ACAD

[5] Enantioselective desymmetrisation of achiral epoxides [J].

Hodgson, DM ;

Gibbs, AR ;

Lee, GP .

TETRAHEDRON, 1996, 52 (46) :14361-14384

[6] MULTIMACROCYCLIC COMPOUNDS .4. INTERNAL TRIMERISATION OF TRIPLE BONDS OF LINEAR TRIYNES ON A ZIEGLER CATALYST [J].

HUBERT, AJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :1984-&

[7] Thiourea-catalyzed enantioselective hydrophosphonylation of imines:: Practical access to enantiomerically enriched α-amino phosphonic acids [J].

Joly, GD ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4102-4103

[8]

Li C. -J., 1997, ORGANIC REACTIONS AQ

[9]

PATTENDEN G, 1991, COMPREHENSIVE ORGANI, V3, P223

[10] Efficient method for cleavage of aziridines with aromatic amines [J].

Sekar, G ;

Singh, VK .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2537-2539

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