The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of α,α-difluoro-β-hydroxy ketones

被引：28

作者：

Balnaves, AS

Gelbrich, T

Hursthouse, MB

Light, ME

Palmer, MJ

Percy, JM ^{[1
]}

机构：

[1] Univ Birmingham, Sch Chem, Birmingham B15 2TT, W Midlands, England

[2] Pfizer Ltd, Cent Res, Sandwich CT13 9NJ, Kent, England

[3] Univ Southampton, Dept Chem, EPSRC Natl Xray Crystallog Serv, Southampton SO17 1BJ, Hants, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 17期

关键词：

D O I：

10.1039/a902966d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Metallated difluoroenol carbamate 1 reacted with aldehydes and ketones in the presence of highly oxophilic Lewis acid boron trifluoride-ethyl ether; the Lewis acid attenuated the transacylation reaction to the corresponding enolates so that allylic alcohols could be isolated. Treatment of the allylic alcohols with strong base afforded difluoroenolates which could be trapped cleanly in aldol reactions.

引用

收藏

页码：2525 / 2535

页数：11

相关论文

共 34 条

[1] EXAMINATION OF PEPTIDIC ALPHA',BETA-DIAMINO-ALPHA,ALPHA-DIFLUOROKETONES AS INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE [J].

BERNSTEIN, PR ;

KOSMIDER, BJ ;

VACEK, EP ;

VEALE, CA ;

GOMES, BC .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (18) :2175-2178

[2]

Braun M, 1998, ANGEW CHEM INT EDIT, V37, P430, DOI 10.1002/(SICI)1521-3773(19980302)37:4<430::AID-ANIE430>3.0.CO

[3]

2-5

[4] Mixed organofluorine-organosilicon chemistry .6. Synthesis of gem-difluoro-C-glycosides and C-disaccharides from acylsilanes and trifluoromethyltrimethylsilane. An exploratory study [J].

Brigaud, T ;

Lefebvre, O ;

PlantierRoyon, R ;

Portella, C .

TETRAHEDRON LETTERS, 1996, 37 (34) :6115-6116

[5] SYNTHESIS OF DIFLUOROENOXYSILANES FROM ACYLSILANES AND TRIFLUOROMETHYLTRIMETHYLSILANE (TFMTMS) - DRAMATIC EFFECT OF THE CATALYTIC FLUORIDE SOURCE [J].

BRIGAUD, T ;

DOUSSOT, P ;

PORTELLA, C .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2117-2118

[6] DESIGN AND SYNTHESIS OF POTENT, SELECTIVE, AND ORALLY ACTIVE FLUORINE-CONTAINING RENIN INHIBITORS [J].

DOHERTY, AM ;

SIRCAR, I ;

KORNBERG, BE ;

QUIN, J ;

WINTERS, RT ;

KALTENBRONN, JS ;

TAYLOR, MD ;

BATLEY, BL ;

RAPUNDALO, SR ;

RYAN, MJ ;

PAINCHAUD, CA .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (01) :2-14

[7] Peptidyl human heart chymase inhibitors. 2. Discovery of highly selective difluoromethylene ketone derivatives with Glu at P3 site [J].

Eda, M ;

Ashimori, A ;

Akahoshi, F ;

Yoshimura, T ;

Inoue, Y ;

Fukaya, C ;

Nakajima, M ;

Fukuyama, H ;

Imada, T ;

Nakamura, N .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (08) :919-924

[8] Peptidyl human heart chymase inhibitors.: 1.: Synthesis and inhibitory activity of difluoromethylene ketone derivatives bearing P′ binding subsites [J].

Eda, M ;

Ashimori, A ;

Akahoshi, F ;

Yoshimura, T ;

Inoue, Y ;

Fukaya, C ;

Nakajima, M ;

Fukuyama, H ;

Imada, T ;

Nakamura, N .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (08) :913-918

[9] MECHANISM AND SYNTHETIC UTILITY OF BORON-TRIFLUORIDE ETHERATE PROMOTED ORGANO-LITHIUM ADDITIONS [J].

EIS, MJ ;

WROBEL, JE ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (12) :3693-3694

[10] NEW FLUORINE-CONTAINING BUILDING-BLOCKS FROM TRIFLUOROETHANOL .2. [J].

HOWARTH, JA ;

OWTON, WM ;

PERCY, JM ;

ROCK, MH .

TETRAHEDRON, 1995, 51 (37) :10289-10302

← 1 2 3 4 →