A CONVENIENT SYNTHESIS OF ALPHA-TRIFLUOROMETHYLATED AND ALPHA-PERFLUOROALKYLATED ACYLOINS FROM ALPHA-HYDROXY ACIDS

被引：10

作者：

KAWASE, M ^{[1
]}

KURIHARA, T ^{[1
]}

机构：

[1] JOSAI UNIV,FAC SCI,SAKADO,SAITAMA 35002,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 44期

关键词：

D O I：

10.1016/0040-4039(94)88284-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel transformation of alpha-hydroxy acids to alpha-trifluoromethylated and alpha-perfluoroalkylated acyloins was efficiently realized by utilizing trifluoroacetic or perfluoroalkylcarboxylic anhydrides in the presence of pyridine, in which probable intermediates were meso-ionic 1,3-dioxolium-4-olates.

引用

收藏

页码：8209 / 8212

页数：4

相关论文

共 21 条

[1] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].

BEGUE, JP ;

BONNETDELPON, D .

TETRAHEDRON, 1991, 47 (20-21) :3207-3258

[2] EFFICIENT PROCEDURE TO 4-CARBETHOXY-3-TRIFLUOROMETHYLCYCLOHEX-2-ENONE AND 4-ALKYLATED DERIVATIVES [J].

BEGUE, JP ;

BONNETDELPON, D ;

DOGBEAVOU, A .

SYNTHETIC COMMUNICATIONS, 1992, 22 (04) :573-579

[3] A VERSATILE SYNTHESIS OF AMINO TRIFLUOROMETHYL KETONES AND ALCOHOLS [J].

BEGUE, JP ;

BONNETDELPON, D ;

SDASSI, H .

TETRAHEDRON LETTERS, 1992, 33 (14) :1879-1882

[4] A NEW FURAN SYNTHESIS - EVIDENCE FOR THE INTERMEDIACY OF THE ELUSIVE ANHYDRO-5-HYDROXY-1,3-DIOXOLIUM HYDROXIDE SYSTEM [J].

BERK, HC ;

ZWIKELMAIER, KE ;

FRANZ, JE .

SYNTHETIC COMMUNICATIONS, 1980, 10 (09) :707-710

[5] AN EXPEDIENT ACCESS TO TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS [J].

BOIVIN, J ;

ELKAIM, L ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1992, 33 (10) :1285-1288

[6] THE DAKIN-WEST REACTION [J].

BUCHANAN, GL .

CHEMICAL SOCIETY REVIEWS, 1988, 17 (02) :91-109

[7] SYNTHESIS OF 3-TRIFLUOROMETHYLFURANS FROM BETA,BETA-BIS(TRIFLUOROMETHYL) ALPHA,BETA-UNSATURATED KETONES AND TIN(II) CHLORIDE [J].

BURGER, K ;

HELMREICH, B .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :348-349

[8] A METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF PEPTIDYL TRIFLUOROMETHYL KETONES [J].

EDWARDS, PD .

TETRAHEDRON LETTERS, 1992, 33 (30) :4279-4282

[9] FORMATION AND REACTIONS OF MESOIONIC ANHYDRO-4-HYDROXY-1,3-DIOXOLIUM HYDROXIDES [J].

HAMAGUCHI, M ;

NAGAI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (04) :190-191

[10]

ISHIKAWA N, 1987, SYNTHESIS SPECIALITY