ASYMMETRIC CATALYSIS .91. ENANTIOSELECTIVE MONOPHENYLATION OF CIS-1,2-CYCLOPENTANEDIOL WITH TRIPHENYLBISMUTH DIACETATE AND CHIRAL COPPER(II) COMPLEXES AS CATALYSTS

被引：10

作者：

BRUNNER, H

CHUARD, T

机构：

[1] Institut für Anorganische Chemie, Universität Regensburg, Regensburg

来源：

MONATSHEFTE FUR CHEMIE | 1994年 / 125卷 / 12期

关键词：

ENANTIOSELECTIVE CATALYSIS; CHIRAL CU(II) COMPLEXES; MONOPHENYLATION; TRIPHENYLBISMUTH DIACETATE; CIS-1,2-CYCLOPENTANEDIOL;

D O I：

10.1007/BF00811078

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The monophenylation of cis-1,2-cyclopentanediol with triphenylbismuth diacetate in the presence of chiral Cu(II) complexes as catalysts gave cis-2-hydroxy-1-phenoxy-cyclopentane with enantiomeric excesses up to 38%. The optically active ligands used were triamine derivatives of 2,6-bis(aminomethyl)pyridine and diamine derivatives of 2-(aminomethyl)pyridine. Selectivity in the monophenylation occurred only in the presence of the latter as auxiliary ligands.

引用

收藏

页码：1293 / 1300

页数：8

相关论文

共 25 条

[1] PENTAVALENT ORGANOBISMUTH REAGENTS .3. PHENYLATION OF ENOLS AND OF ENOLATE AND OTHER ANIONS [J].

BARTON, DHR ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2667-2675

[2] PENTAVALENT ORGANOBISMUTH REAGENTS .2. THE PHENYLATION OF PHENOLS [J].

BARTON, DHR ;

BHATNAGAR, NY ;

BLAZEJEWSKI, JC ;

CHARPIOT, B ;

FINET, JP ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB ;

STANFORTH, SP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2657-2665

[3] THE CATALYTIC EFFECT OF COPPER IONS IN THE PHENYLATION REACTION OF DAVID AND THIEFFRY [J].

BARTON, DHR ;

FINET, JP ;

PICHON, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (01) :65-66

[4] PENTAVALENT ORGANOBISMUTH REAGENTS .6. COMPARATIVE MIGRATORY APTITUDES OF ARYL GROUPS IN THE ARYLATION OF PHENOLS AND ENOLS BY PENTAVALENT BISMUTH REAGENTS [J].

BARTON, DHR ;

BHATNAGAR, NY ;

FINET, JP ;

MOTHERWELL, WB .

TETRAHEDRON, 1986, 42 (12) :3111-3122

[5] COPPER-SALTS CATALYSIS OF N-PHENYLATION OF AMINES BY TRIVALENT ORGANOBISMUTH COMPOUNDS [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1987, 28 (08) :887-890

[6] COPPER CATALYZED PHENYLATION OF INDOLES BY TRIPHENYLBISMUTH BIS-TRIFLUOROACETATE [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1988, 29 (10) :1115-1118

[7] METALLIC COPPER CATALYSIS OF N-ARYLATION OF AMINES BY TRIARYLBISMUTH DIACYLATES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1986, 27 (31) :3615-3618

[8] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .8. PHENYLATION AND OXIDATION OF ALCOHOLS BY TETRAPHENYLBISMUTH ESTERS [J].

BARTON, DHR ;

FINET, JP ;

MOTHERWELL, WB ;

PICHON, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :251-259

[9] N-PHENYLATION OF AMINO-ACID DERIVATIVES [J].

BARTON, DHR ;

FINET, JP ;

KHAMSI, J .

TETRAHEDRON LETTERS, 1989, 30 (08) :937-940

[10] THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].

BARTON, DHR ;

FINET, JP ;

GIANNOTTI, C ;

HALLEY, F .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249