Difluorinated Danishefsky's diene:: A versatile C4 building block for the fluorinated six-membered rings

被引:81
作者
Amii, H [1 ]
Kobayashi, T [1 ]
Terasawa, H [1 ]
Uneyama, K [1 ]
机构
[1] Okayama Univ, Fac Engn, Dept Appl Chem, Okayama 7008530, Japan
关键词
D O I
10.1021/ol0163631
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A Mg(0)/Me3SiCl system was found to be effective for the preparation of difluoro Danishefsky's dienes 2, which involves selective C-F bond cleavage of trifluoromethyl ketones 3. Subsequent hetero Diels-Alder reactions of 2 with aldehydes and imines gave a variety of fluorinated six-membered heterocycles.
引用
收藏
页码:3103 / 3105
页数:3
相关论文
共 32 条
[1]   Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].
Amii, H ;
Kobayashi, T ;
Hatamoto, Y ;
Uneyama, K .
CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324
[2]  
Amii H, 2000, SYNTHESIS-STUTTGART, P2001
[3]   Dynamics of bond breaking in ion radicals. Mechanisms and reactivity in the reductive cleavage of carbon-fluorine bonds of fluoromethylarenes [J].
Andrieux, CP ;
Combellas, C ;
Kanoufi, F ;
Saveant, JM ;
Thiebault, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (40) :9527-9540
[4]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[5]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 2-SULFONAMIDO- AND 2-SULFAMIDO-1,3,4,6,7,11BALPHA-HEXAHYDRO-2H-BENZO[A]QUINOLIZINES [J].
ARCHIBALD, JL ;
BEARDSLEY, DR ;
WARD, TJ ;
WATERFALL, JF ;
WHITE, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (03) :416-420
[6]  
Cavel P., 1999, SYNTHESIS-STUTTGART, P829
[7]  
CHAUSSARD J, 1990, SYNTHESIS-STUTTGART, P369
[8]  
COLLA A, 1991, SYNTHESIS-STUTTGART, P483
[9]   Synthesis of 2-CF3-tetrahydroquinoline and quinoline derivatives from CF3-N-aryl-aldimine [J].
Crousse, B ;
Bégué, JP ;
Bonnet-Delpon, D .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :5009-5013
[10]   SILOXY DIENES IN TOTAL SYNTHESIS [J].
DANISHEFSKY, S .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (12) :400-406