Electrophilic fluorodesilylation of allenylmethylsilanes: A novel entry to 2-fluoro-1,3-dienes

被引:44
作者
Pacheco, MC [1 ]
Gouverneur, V [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
关键词
D O I
10.1021/ol047319z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various fluorodienes were prepared by treatment of the corresponding allenylmethylsilanes with Selectfluor. This is the first route to these compounds not based on the use of a fluorinated building block. The reaction allows the preparation of 2-fluoro-1,3-dienes with several substitution patterns, including di- and trisubstituted compounds.
引用
收藏
页码:1267 / 1270
页数:4
相关论文
共 50 条
[1]   Cobalt-catalyzed cycloisomerization of 1,6-enynes and allyl propargyl ethers [J].
Ajamian, A ;
Gleason, JL .
ORGANIC LETTERS, 2003, 5 (14) :2409-2411
[2]   RING-OPENING OF GEM-DIHALOCYCLOPROPANES - NOVEL TYPES OF 1,4-ELIMINATION REACTIONS [J].
BESSARD, Y ;
KUHLMANN, L ;
SCHLOSSER, M .
TETRAHEDRON, 1990, 46 (15) :5230-5236
[3]   Diastereocontrol in open-chain nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group [J].
Betson, MS ;
Fleming, I ;
Ouzman, JVA .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (22) :4017-4024
[4]   Accurate determinations of the extent to which the SE2′ reactions of allyl-, allenyl- and propargylsilanes are stereospecifically anti [J].
Buckle, MJC ;
Fleming, I ;
Gil, S ;
Pang, KLC .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (05) :749-769
[5]   ACCURATE DETERMINATION OF THE EXTENT TO WHICH THE S(E)2' REACTIONS OF AN ALLENYLSILANE ARE STEREOSPECIFICALLY ANTI [J].
BUCKLE, MJC ;
FLEMING, I .
TETRAHEDRON LETTERS, 1993, 34 (14) :2383-2386
[6]   Allylsilanes in organic synthesis - Recent developments [J].
Chabaud, L ;
James, P ;
Landais, Y .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (15) :3173-3199
[7]   BETA-LACTAMS FROM ALLYL-SILANES AND (ALLENYLMETHYL)-SILANES [J].
COLVIN, EW ;
MONTEITH, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (18) :1230-1232
[8]   DIASTEREOSELECTIVE FLUORINATION OF CHIRAL IMIDE ENOLATES USING N-FLUORO-O-BENZENEDISULFONIMIDE (NFOBS) [J].
DAVIS, FA ;
HAN, W .
TETRAHEDRON LETTERS, 1992, 33 (09) :1153-1156
[9]   SELECTIVE, ELECTROPHILIC FLUORINATIONS USING N-FLUORO-O-BENZENEDISULFONIMIDE [J].
DAVIS, FA ;
HAN, W ;
MURPHY, CK .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4730-4737
[10]   N-FLUORO-ORTHO-BENZENEDISULFONIMIDE - A USEFUL NEW FLUORINATING REAGENT [J].
DAVIS, FA ;
HAN, W .
TETRAHEDRON LETTERS, 1991, 32 (13) :1631-1634