ENANTIOSELECTIVE, ELECTROCATALYTIC OXIDATIVE COUPLING OF NAPHTHOL, NAPHTHYL ETHER AND PHENANTHROL ON A TEMPO-MODIFIED GRAPHITE FELT ELECTRODE IN THE PRESENCE OF (-)-SPARTEINE (TEMPO=2,2,6,6-TETRAMETHYLPIPEERIDIN-1-YLOXYL)

被引：95

作者：

OSA, T ^{[1
]}

KASHIWAGI, Y ^{[1
]}

YANAGISAWA, Y ^{[1
]}

BOBBITT, JM ^{[1
]}

机构：

[1] UNIV CONNECTICUT,DEPT CHEM,STORRS,CT 06269

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1994年 / 21期

关键词：

D O I：

10.1039/c39940002535

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Constant potential electrolysis of 2-naphthol, 2-methoxynaphthalene and 10-hydroxyphenanthrene at 0.6V vs. Ag/AgCl on a TEMPO-modified graphite felt electrode in the presence of (-)-sparteine in acetonitrile yields, enantioselectively, (S)-binaphthyl type dimers in >92% isolated yield and with >88% current efficiency with enantiomeric excesses of 98, 91 and 97% respectively for each dimer, respectively.

引用

收藏

页码：2535 / 2537

页数：3

相关论文

共 16 条

[1]

BOBBITT JM, 1992, HETEROCYCLES, V33, P641

[2] ON THE MECHANISM OF THE FORMATION OF "S(-)-(1,1'-BINAPHTHALENE)-2,2'-DIOL VIA COPPER(II)AMINE COMPLEXES [J].

BRUSSEE, J ;

GROENENDIJK, JLG ;

TEKOPPELE, JM ;

JANSEN, ACA .

TETRAHEDRON, 1985, 41 (16) :3313-3319

[3] ELECTROCATALYTIC OXIDATIVE COUPLING REACTION OF NAPHTHOLS AND NAPHTHOL ETHERS ON A TEMPO MODIFIED GRAPHITE FELT ELECTRODE [J].

KASHIWAGI, Y ;

ONO, H ;

OSA, T .

CHEMISTRY LETTERS, 1993, (01) :81-84

[4] ELECTROCATALYTIC OXIDATIVE COUPLING OF METHYLQUINOLINES ON TEMPO-MODIFIED GRAPHITE FELT ELECTRODES [J].

KASHIWAGI, Y ;

ONO, H ;

OSA, T .

CHEMISTRY LETTERS, 1993, (02) :257-260

[5] HOST-GUEST COMPLEXATION .23. HIGH CHIRAL RECOGNITION OF AMINO-ACID AND ESTER GUESTS BY HOSTS CONTAINING ONE CHIRAL ELEMENT [J].

LINGENFELTER, DS ;

HELGESON, RC ;

CRAM, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :393-406

[6] ORGANIC OXOAMMONIUM SALTS .3. A NEW CONVENIENT METHOD FOR THE OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES [J].

MA, Z ;

BOBBITT, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6110-6114

[7] ENANTIOSELECTIVE SYNTHESIS OF BINAPHTHYLS VIA NUCLEOPHILIC AROMATIC-SUBSTITUTION ON CHIRAL OXAZOLINES [J].

MEYERS, AI ;

LUTOMSKI, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (03) :879-881

[8] ASYMMETRIC-SYNTHESIS OF AXIALLY DISSYMMETRIC 1,1'-BINAPHTHYLS VIA AN INTRAMOLECULAR ULLMANN COUPLING REACTION OF (R) AND (S)-2,2'-BIS(1-BROMO-2-NAPHTHYLCARBONYLOXY)-1,1'-BINAPHTHYL [J].

MIYANO, S ;

TOBITA, M ;

HASHIMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (11) :3522-3526

[9]

NARASAKA K, 1991, SYNTHESIS-STUTTGART, P1

[10] CHROMATOGRAPHIC RESOLUTION .4. NOVEL PACKING MATERIAL FOR OPTICAL RESOLUTION - (+)-POLY(TRIPHENYLMETHYL METHACRYLATE) COATED ON MACROPOROUS SILICA-GEL [J].

OKAMOTO, Y ;

HONDA, S ;

OKAMOTO, I ;

YUKI, H ;

MURATA, S ;

NOYORI, R ;

TAKAYA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (23) :6971-6973