Mixed organofluorine-organosilicon chemistry. 8. One-pot synthesis of 2,2-difluoro-1,5 diketones from acylsilanes, trifluoromethyltrimethylsilane and enones, and their annulation reaction

被引:67
作者
Lefebvre, O [1 ]
Brigaud, T [1 ]
Portella, C [1 ]
机构
[1] Univ Reims, Fac Sci, Lab React Select & Applicat, CNRS UMR 6519, F-51687 Reims 2, France
关键词
D O I
10.1016/S0040-4020(98)00224-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe the synthesis of 2,2-difluoro-1,5-diketones in a one-pot procedure from an acylsilane and trifluoromethyltrimethylsilane, via reaction of difluoroenoxysilanes and enones under electrophilic activation. These diketones are interesting building blocks for the synthesis of gem-difluoro enones or substituted fluorophenols, depending on the annulation conditions. The annulation proceeds with complete regioselectivity controlled by the fluorine substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.
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页码:5939 / 5948
页数:10
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共 18 条
[1]   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
[2]   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
[3]   SYNTHESIS OF SILYL AND GERMYL KETONES [J].
BROOK, AG ;
DUFF, JM ;
NONES, PF ;
DAVIS, NR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :431-&
[4]   SYNTHESIS OF ALPHA-SILYL KETONES VIA 1,3-DITHIANES [J].
COREY, EJ ;
SEEBACH, D ;
FREEDMAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :434-&
[5]   LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE [J].
DUHAMEL, P ;
DUJARDIN, G ;
HENNEQUIN, L ;
POIRIER, JM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03) :387-396
[6]   TETRABUTYLAMMONIUM DIFLUOROTRIPHENYLSTANNATE AS A NEW ANHYDROUS SYNTHETIC EQUIVALENT TO TBAF [J].
GINGRAS, M .
TETRAHEDRON LETTERS, 1991, 32 (50) :7381-7384
[7]   TRIFLUOROACETYLTRIPHENYLSILANE AS A POTENTIALLY USEFUL FLUORINE-CONTAINING BUILDING BLOCK - PREPARATION AND ITS TRANSFORMATION INTO 2,2-DIFLUORO ENOL SILYL ETHERS [J].
JIN, FQ ;
JIANG, BA ;
XU, YY .
TETRAHEDRON LETTERS, 1992, 33 (09) :1221-1224
[8]   LANTHANIDE TRIFLUOROMETHANESULFONATES AS REUSABLE CATALYSTS - CATALYTIC FRIEDEL-CRAFTS ACYLATION [J].
KAWADA, A ;
MITAMURA, S ;
KOBAYASHI, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (14) :1157-1158
[9]   THE ALDOL REACTION OF SILYL ENOL ETHERS WITH ALDEHYDES IN AQUEOUS-MEDIA [J].
KOBAYASHI, S ;
HACHIYA, I .
TETRAHEDRON LETTERS, 1992, 33 (12) :1625-1628
[10]   LANTHANIDE TRIFLUOROMETHANESULFONATES AS REUSABLE CATALYSTS - MICHAEL AND DIELS-ALDER REACTIONS [J].
KOBAYASHI, S ;
HACHIYA, I ;
TAKAHORI, T ;
ARAKI, M ;
ISHITANI, H .
TETRAHEDRON LETTERS, 1992, 33 (45) :6815-6818