Regioselective synthesis of 2,2-dimethylcyclopentanone using 2-pyrrolidone magnesium salt as electrogenerated base.

被引：6

作者：

Bonafoux, D ^{[1
]}

Bordeau, M ^{[1
]}

Biran, C ^{[1
]}

Dunogues, J ^{[1
]}

机构：

[1] Univ Bordeaux 1, Chim Organ & Organomet Lab, CNRS, F-33405 Talence, France

来源：

SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 01期

关键词：

D O I：

10.1080/00397919808005077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, direct and regioselective preparation of 2,2-dimethylcyclopentanone, via its enolate precursor regioselectively obtained using the 2-pyrrolidone magnesium salt, a base electrogenerated in DME/HMPA, is reported.

引用

页码：93 / 98

页数：6

共 17 条

[1] REGIOSPECIFIC ALKYLATION OF ENOLATE IONS IN LIQUID AMMONIA-TETRAHYDROFURAN [J].

BINKLEY, ES ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (15) :2156-2160

[2] STEREOSELECTIVE ELECTROCHEMICAL SYNTHESIS OF SILYL ENOL ETHERS USING A SACRIFICIAL MAGNESIUM ANODE [J].

BONAFOUX, D ;

BORDEAU, M ;

BIRAN, C ;

DUNOGUES, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 493 (1-2) :27-32

[3] Regio- and stereoselective synthesis of silyl enol ethers using a new base electrogenerated from hexamethyldisilazane [J].

Bonafoux, D ;

Bordeau, M ;

Biran, C ;

Cazeau, P ;

Dunogues, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5532-5536

[4]

Caine D., 1991, COMPREHENSIVE ORGANI

[5] SITE-SELECTIVE GEMINAL ALKYLATION OF KETONES - REDUCTION-ALKYLATION OF BURYLTHIOMETHYLENE DERIVATIVES [J].

COATES, RM ;

SOWERBY, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (04) :1027-&

[6] KETONE ENOLATES - REGIOSPECIFIC PREPARATION AND SYNTHETIC USES [J].

DANGELO, J .

TETRAHEDRON, 1976, 32 (24) :2979-2990

[7] HOMOGENEOUS CATALYSIS - CONVERSION OF 4-PENTENALS TO CYCLOPENTANONES BY EFFICIENT RHODIUM-CATALYZED HYDROACYLATION [J].

FAIRLIE, DP ;

BOSNICH, B .

ORGANOMETALLICS, 1988, 7 (04) :936-945

[8] CHEMISTRY OF CARBANIONS .19. ALKYLATION OF ENOLATES FROM UNSYMMETRICAL KETONES [J].

HOUSE, HO ;

GALL, M ;

OLMSTEAD, HD .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (16) :2361-&

[9]

HOUSE HO, 1972, MODERN SYNTHETIC REA, P492

[10] STRUCTURE AND REACTIVITY OF ALKALI-METAL ENOLATES [J].

JACKMAN, LM ;

LANGE, BC .

TETRAHEDRON, 1977, 33 (21) :2737-2769

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