STEREOSELECTIVITY OF CYCLOADDITION OF N-(CYANOMETHYL)IMINES AND N-(ALPHA-CYANOBENZYL)IMINES WITH OLEFINIC DIPOLAROPHILES - SYNTHETIC EQUIVALENTS OF NITRILE YLIDE 1,3-DIPOLES

被引：72

作者：

TSUGE, O ^{[1
]}

UENO, K ^{[1
]}

KANEMASA, S ^{[1
]}

YOROZU, K ^{[1
]}

机构：

[1] KYUSHU UNIV, INTERDISCIPLINARY GRAD SCH ENGN SCI, DEPT MOLEC SCI & TECHNOL, KASUGA, FUKUOKA 816, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1986年 / 59卷 / 06期

关键词：

Cyanides; -; Cycloaddition; Ketones;

D O I：

10.1246/bcsj.59.1809

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-(Cyanomethyl)- and N-(a-cyanobenzyl)imines derived from a variety of aldehydes and ketones can tauto-merize into iV-protonated azomethine ylides which undergo cycloadditions with olefinic dipolarophiles. These cycloadditions are often accompanied by the elimination of HCN, mostly in a stereospecific manner, showing these imines to be synthetic equivalents of nonstabilized nitrile ylides. Stereoselectivity of the cycloadditions is discussed. © 1986 The Chemical Society of Japan.

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页码：1809 / 1824

页数：16

相关论文

共 30 条

[1] 1,3-DIPOLAR CYCLO-ADDITIONS OF 6,7-DIALKOXY-3,4-DIHYDROISOQUINOLINIUM SALTS [J].

BENDE, Z ;

TOKE, L ;

WEBER, L ;

TOTH, G ;

JANKE, F ;

CSONKA, G .

TETRAHEDRON, 1984, 40 (02) :369-375

[2] METHYL-ALPHA-BROMOACRYLATE, A BICYCLIZATION REAGENT IN A HETEROCYCLIC SERIES - PREPARATION OF 1-AZA-(2,1,0)-BICYCLOPENTANES [J].

FOUCHET, B ;

JOUCLA, M ;

HAMELIN, J .

TETRAHEDRON LETTERS, 1981, 22 (35) :3397-3400

[3]

GILGEN P, 1977, HETEROCYCLES, V6, P143

[4] DECARBOXYLATIVE TRANSAMINATION - MECHANISM AND APPLICATIONS TO THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].

GRIGG, R ;

THIANPATANAGUL, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :180-181

[5] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .1. BACKGROUND AND SCOPE [J].

GRIGG, R ;

GUNARATNE, HQN ;

KEMP, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (01) :41-46

[6] BRONSTED AND LEWIS ACID CATALYSIS OF X=Y-ZH CYCLO-ADDITIONS [J].

GRIGG, R ;

GUNARATNE, HQN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (07) :384-386

[7] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES - THE STEREOCHEMISTRY AND REGIOCHEMISTRY OF CYCLOADDITION REACTIONS OF IMINES OF ALPHA-AMINO-ACID ESTERS [J].

GRIGG, R ;

KEMP, J .

TETRAHEDRON LETTERS, 1980, 21 (25) :2461-2464

[8]

GRIGG R, 1984, B SOC CHIM BELG, V93, P593

[9] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES - CYCLO-ADDITIONS OF THIOIMINOETHERS AND THIOIMINOCARBONATES [J].

GRIGG, R ;

BASANAGOUDAR, LD ;

KENNEDY, DA ;

MALONE, JF ;

THIANPATANAGUL, S .

TETRAHEDRON LETTERS, 1982, 23 (27) :2803-2806

[10]

Grigg R., 1978, CHEM COMMUN, P109