Asymmetric ring opening of epoxides

被引：146

作者：

Pastor, IM

Yus, M

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, E-03080 Alicante, Spain

[2] Univ Alicante, ISO, E-03080 Alicante, Spain

来源：

CURRENT ORGANIC CHEMISTRY | 2005年 / 9卷 / 01期

关键词：

D O I：

10.2174/1385272053369385

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review deals with the metal promoted asymmetric ring opening of achiral epoxides using achiral carbon-, nitrogen-, oxygen-, sulphur- and halogen-containing nucleophiles. The use of chiral bases in the asymmetric deprotonation of achiral epoxides yields chiral allylic alcohols. Finally, kinetic resolution of racemic epoxides can be achieved using chiral metal complexes.

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页码：1 / 29

页数：29

相关论文

共 132 条

[1] CHIRAL LEWIS-ACID CATALYZED ASYMMETRIC NUCLEOPHILIC RING-OPENING OF CYCLOHEXENE OXIDE [J].

ADOLFSSON, H ;

MOBERG, C .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :2023-2031

[2] Comparison of amine additives most effective in the new methyltrioxorhenium-catalyzed epoxidation process [J].

Adolfsson, H ;

Converso, A ;

Sharpless, KB .

TETRAHEDRON LETTERS, 1999, 40 (21) :3991-3994

[3]

Amedjkouh M, 2001, CHEM-EUR J, V7, P4368, DOI 10.1002/1521-3765(20011015)7:20<4368::AID-CHEM4368>3.0.CO

[4]

2-K

[5]

Annis DA, 1998, ANGEW CHEM INT EDIT, V37, P1907, DOI 10.1002/(SICI)1521-3773(19980803)37:13/14<1907::AID-ANIE1907>3.0.CO

[6]

2-A

[7] Polymer-supported chiral Co(salen) complexes: Synthetic applications and mechanistic investigations in the hydrolytic kinetic resolution of terminal epoxides [J].

Annis, DA ;

Jacobsen, EN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4147-4154

[8] A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides [J].

Asami, M ;

Suga, T ;

Honda, K ;

Inoue, S .

TETRAHEDRON LETTERS, 1997, 38 (36) :6425-6428

[9] An intriguing effect of polymer-bound lithium amides in catalytic enantioselective rearrangement of meso-epoxides mediated by chiral lithium amides [J].

Asami, M ;

Seki, A .

CHEMISTRY LETTERS, 2002, (02) :160-161

[10] Kinetic resolution of cis-3-alkylcyclohexene oxide by a chiral lithium amide -: An application to a synthesis of both enantiomers of isomenthone [J].

Asami, M ;

Sato, S ;

Honda, K ;

Inoue, S .

HETEROCYCLES, 2000, 52 (03) :1029-+

← 1 2 3 4 5 6 7 8 9 10 →