LITHIUM BENZENETELLUROLATE-INDUCED REFORMATSKY-TYPE REACTION IN THE PRESENCE OF CERIUM TRICHLORIDE

被引：8

作者：

FUKUZAWA, S

HIRAI, K

机构：

[1] Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, Bunkyo-ku

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930001963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reformatsky-type reactions with PhTeLi in the presence of CeCl3 proceeded smoothly under mild conditions. The PhTeLi-CeCl3 reagent was particularly efficient for the reactions of sterically hindered and enolizable ketones; in the absence of CeCl3 unsatisfactory yields of the desired beta-hydroxy ketone were obtained. It is assumed that CeCl3 reactions involve a cerium enolate intermediate. The stereoselectivity of the reaction between ethyl 2-bromopropionate and benzaldehyde is also described.

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页码：1963 / 1965

页数：3

相关论文

共 16 条

[1] CHROMIUM(II) CHLORIDE - A NEW REAGENT FOR CROSS-ALDOL REACTIONS [J].

DUBOIS, JE ;

AXIOTIS, G ;

BERTOUNESQUE, E .

TETRAHEDRON LETTERS, 1985, 26 (36) :4371-4372

[2] ORGANOTELLURIUM CHEMISTRY .7. REDUCTIVE REMOVAL OF ELECTRONEGATIVE ALPHA-SUBSTITUENTS OF KETONES AND ACIDS BY A TELLUROLATE REAGENT [J].

ENGMAN, L ;

CAVA, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (20) :3946-3949

[3] REACTION OF ALPHA-HALOGENO KETONES WITH CARBONYL-COMPOUNDS PROMOTED BY CEL3, CECL3-NAL, OR CECL3-SNCL2 [J].

FUKUZAWA, S ;

TSURUTA, T ;

FUJINAMI, T ;

SAKAI, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (07) :1473-1477

[4]

FURSTNER A, 1989, SYNTHESIS-STUTTGART, P571

[5] A NEW METHOD FOR THE SYNTHESIS OF BETA-HYDROXYESTERS BY USING METALLIC TIN [J].

HARADA, T ;

MUKAIYAMA, T .

CHEMISTRY LETTERS, 1982, (02) :161-164

[6]

HARADA T, 1982, CHEM LETT, P462

[7] THE STUDIES OF THE APPLICATION OF ELEMENTO-ORGANIC COMPOUNDS OF THE 15TH AND 16TH GROUPS IN ORGANIC-SYNTHESIS .60. BETA-HYDROXY KETONES FROM THE IODINE-CATALYZED REACTION OF ALPHA-BROMO KETONE WITH ALDEHYDES MEDIATED BY TRIALKYLSTIBINE [J].

HUANG, YZ ;

CHEN, C ;

SHEN, YC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10) :2855-2859

[8] CARBON CARBON BOND-FORMING REACTIONS USING CERIUM METAL OR ORGANOCERIUM(III) REAGENTS [J].

IMAMOTO, T ;

KUSUMOTO, T ;

TAWARAYAMA, Y ;

SUGIURA, Y ;

MITA, T ;

HATANAKA, Y ;

YOKOYAMA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3904-3912

[9] A NEW ALDOL REACTION VIA CERIUM ENOLATES [J].

IMAMOTO, T ;

KUSUMOTO, T ;

YOKOYAMA, M .

TETRAHEDRON LETTERS, 1983, 24 (47) :5233-5236

[10]

IMAMOTO T, 1991, ORGANOCERIUM REAGENT, V1, P231