Asymmetric epoxidation of olefins catalyzed by chiral iminium salts generated in situ from amines and aldehydes

被引：63

作者：

Wong, MK ^{[1
]}

Ho, LM ^{[1
]}

Zheng, YS ^{[1
]}

Ho, CY ^{[1
]}

Yang, D ^{[1
]}

机构：

[1] Univ Hong Kong, Dept Chem, Hong Kong, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 16期

关键词：

D O I：

10.1021/ol016260i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new approach for catalytic asymmetric epoxidation of olefins was developed that utilized chiral iminium salts, generated in situ from chiral amines and aldehydes, as catalysts. Epoxidation reactions can be conducted with 20 mol % of amines and aldehydes. The enantioselectivity of epoxides can be up to 65%. This modular approach obviates the difficulties inherent in the preparation and isolation of unstable exocyclic iminium salts.

引用

页码：2587 / 2590

页数：4

共 15 条

[1] Epoxidation of alkenes by amine catalyst precursors: Implication of aminium ion and radical cation intermediates [J].

Adamo, MFA ;

Aggarwal, VK ;

Sage, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8317-8318

[2]

AGGARWAL VK, 1996, J CHEM SOC CHEM COMM, P191

[3] Exocyclic iminium salts as catalysts for alkene epoxidation by Oxone® [J].

Armstrong, A ;

Ahmed, G ;

Garnett, I ;

Goacolou, K ;

Wailes, JS .

TETRAHEDRON, 1999, 55 (08) :2341-2352

[4] Oxygen atom transfer from a chiral oxaziridinium salt.: Asymmetric epoxidation of unfunctionalized olefins. [J].

Bohé, L ;

Lusinchi, M ;

Lusinchi, X .

TETRAHEDRON, 1999, 55 (01) :141-154

[5] THE STEREOSPECIFIC SYNTHESIS OF A NEW CHIRAL OXAZIRIDINIUM SALT [J].

BOHE, L ;

HANQUET, G ;

LUSINCHI, M ;

LUSINCHI, X .

TETRAHEDRON LETTERS, 1993, 34 (45) :7271-7274

[6] OXYGEN-TRANSFER FROM AN OXAZIRIDINIUM SALT TO AN ETHYLENIC DOUBLE-BOND [J].

HANQUET, G ;

LUSINCHI, X ;

MILLIET, P .

TETRAHEDRON LETTERS, 1988, 29 (32) :3941-3944

[7]

Jacobsen E. N., 1999, COMPREHENSIVE ASYMME, V2, P649

[8]

Job P, 1928, ANN CHIM FRANCE, V9, P113

[9]

Johnson R.A., 1993, CATALYTIC ASYMMETRIC

[10]

Katsuki T., 1999, COMPREHENSIVE ASYMME, V2, P621

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