Tetrakis(dimethylamino)ethylene (TDAE) as a useful reductant of some chlorodifluoromethylated ketones.: A new approach for the synthesis of α,α-difluoroketone derivatives.

被引：28

作者：

Burkholder, C

Dolbier, WR

Medebielle, M

Ndedi, A

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

[2] Univ Denis Diderot, Electrochim Mol Lab, CNRS, F-75251 Paris 05, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 48期

关键词：

D O I：

10.1016/S0040-4039(98)02028-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetrakis(dimethylamino)ethylene (TDAE) was found to be an effective reductant of chlorodifluoromethylated ketones 1-3. The generated alpha,alpha-difluoroacetyl anion was trapped with several aldehydes 4-7, under mild conditions, to give the corresponding 2,2-difluoro-3-hydroxy ketone derivatives 8-13, in moderate yields. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：8853 / 8856

页数：4

共 21 条

[1] GENERAL-SYNTHESIS OF POLYFUNCTIONALIZED FLUOROMETHYLENEKETONE RETROAMIDES AS POTENTIAL INHIBITORS OF THROMBIN
ALTENBURGER, JM
SCHIRLIN, D
[J]. TETRAHEDRON LETTERS, 1991, 32 (49) : 7255 - 7258
[2] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES
BEGUE, JP
BONNETDELPON, D
[J]. TETRAHEDRON, 1991, 47 (20-21) : 3207 - 3258
[3] EXAMINATION OF PEPTIDIC ALPHA',BETA-DIAMINO-ALPHA,ALPHA-DIFLUOROKETONES AS INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE
BERNSTEIN, PR
KOSMIDER, BJ
VACEK, EP
VEALE, CA
GOMES, BC
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (18) : 2175 - 2178
[4] Tetrakis(dimethylamino)ethylene as a useful reductant of some bromodifluoromethyl heterocycles.: Application to the synthesis of new gem-difluorinated heteroarylated compounds
Burkholder, C
Dolbier, WR
Médebielle, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (16) : 5385 - 5394
[5] Reaction of the 2(bromodifluoromethyl)benzoxazole with tetrakis(dimethylamino)ethylene (TDAE) in the presence of aldehydes. A convenient synthesis of 2-(difluoromethyl)benzoxazole alcohols.
Burkholder, C
Dolbier, WR
Medebielle, M
[J]. TETRAHEDRON LETTERS, 1997, 38 (05) : 821 - 824
[6] PREPARATION OF ALPHA,ALPHA-DIFLUORO-BETA-HYDROXY ESTERS VIA A MODIFIED REFORMATSKY REACTION
CURRAN, TT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) : 6360 - 6363
[7] SYNTHESIS OF NEW TETRAFLUOROBENZO HETEROAROMATIC-COMPOUNDS
DOLBIER, WR
BURKHOLDER, C
ABBOUD, KA
LOEHLE, D
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) : 7688 - 7694
[8] Synthesis of imidazo[1,2-a]pyridine C-nucleosides with an unexpected site of ribosylation
Gudmundsson, KS
Drach, JC
Townsend, LB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) : 3453 - 3459
[9] 2,2-DIFLUORO-3-HYDROXYESTERS BY REFORMATSKII REACTION
HALLINAN, EA
FRIED, J
[J]. TETRAHEDRON LETTERS, 1984, 25 (22) : 2301 - 2302
[10] NEW LOW-VALENT TITANIUM CATALYZED REACTION OF CHLORODIFLUOROMETHYL KETONES LEADING TO ALPHA,ALPHA-DIFLUORINATED BETA-HYDROXY KETONES
ISHIHARA, T
YAMANAKA, T
ANDO, T
[J]. CHEMISTRY LETTERS, 1984, (07) : 1165 - 1168

← 1 2 3 →