Synthesis and application in asymmetric synthesis of azacrown ethers derived from D-glucose

被引：46

作者：

Bakó, P

Vizvárdi, K

Bajor, Z

Toke, L ^{[1
]}

机构：

[1] Tech Univ Budapest, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary

[2] Tech Univ Budapest, Dept Organ Chem Technol, H-1521 Budapest, Hungary

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 11期

关键词：

D O I：

10.1039/a802098a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New chiral monoaza-15-crown-5 derivatives and lariat ethers anellated to phenyl beta-D-glucoside have been synthesized which show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (84% ee) and in the Darzens condensation of phenacyl chloride with benzaldehyde (74% ee).

引用

页码：1193 / 1194

页数：2

共 8 条

[1] Novel monoaza- and diazacrown ethers incorporating sugar units and their extraction ability towards picrate salts [J].

Bako, P ;

Toke, L .

JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1995, 23 (03) :195-201

[2]

Bako P, 1997, HETEROATOM CHEM, V8, P333, DOI 10.1002/(SICI)1098-1071(1997)8:4<333::AID-HC8>3.0.CO

[3]

2-B

[4]

DICESARE P, 1979, SYNTHETIC COMMUN, P4581

[5] LARIAT ETHERS - FROM SIMPLE SIDEARMS TO SUPRAMOLECULAR SYSTEMS [J].

GOKEL, GW .

CHEMICAL SOCIETY REVIEWS, 1992, 21 (01) :39-47

[6] ABSOLUTE-CONFIGURATION OF CHALCONE EPOXIDE - CHEMICAL CORRELATION [J].

MARSMAN, B ;

WYNBERG, H .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2312-2314

[7] Asymmetric Michael addition and deracemization of enolate by chiral crown ether [J].

Töke, L ;

Bakó, P ;

Keseru, GM ;

Albert, M ;

Fenichel, L .

TETRAHEDRON, 1998, 54 (1-2) :213-222

[8] ASYMMETRIC MICHAEL REACTION - DERACEMIZATION OF ENOLATE BY CHIRAL CROWN-ETHER [J].

TOKE, L ;

FENICHEL, L ;

ALBERT, M .

TETRAHEDRON LETTERS, 1995, 36 (33) :5951-5954

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