Rhodium-catalyzed novel trifluoromethylation at the α-position of α-β-unsaturated ketones

被引:52
作者
Sato, K [1 ]
Omote, M [1 ]
Ando, A [1 ]
Kumadaki, I [1 ]
机构
[1] Setsunan Univ, Fac Pharmaceut Sci, Hirakata, Osaka 5730101, Japan
关键词
D O I
10.1021/ol048134v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of alpha,beta-unsaturated ketones with CF3I in the presence of Et2Zn and RhCl(PPh3)(3) gave novel alpha-trifluoromethylation products in good yields. Hydrogen transfer from the ethyl group on the rhodium complex to the beta-position of the enone seems to play an important role in this reaction.
引用
收藏
页码:4359 / 4361
页数:3
相关论文
共 29 条
[1]  
[Anonymous], 1998, TRANSITION METALS OR
[2]   Desymmetrization of enone-diones via rhodium-catalyzed diastereo- and enantioselective tandem conjugate addition-aidol cyclization [J].
Bocknack, BM ;
Wang, LC ;
Krische, MJ .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5421-5424
[3]   A REMARKABLY SIMPLE PREPARATION OF (TRIFLUOROMETHYL)CADMIUM AND (TRIFLUOROMETHYL) ZINC REAGENTS DIRECTLY FROM DIFLUORODIHALOMETHANES [J].
BURTON, DJ ;
WIEMERS, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (17) :5014-5015
[4]   PHOTOCHEMISTRY OF 6-TRIFLUOROMETHYL-4,4-DIMETHYL-2-CYCLOHEXENONE [J].
CRUCIANI, G ;
MARGARETHA, P .
JOURNAL OF FLUORINE CHEMISTRY, 1987, 37 (01) :95-101
[5]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[6]  
Filler R., 1993, ORGANOFLUORINE COMPO
[7]   The first general method for α-trifluoromethylation of carboxylic acids using BrF3 [J].
Hagooly, A ;
Rozen, S .
CHEMICAL COMMUNICATIONS, 2004, (05) :594-595
[8]  
Hayashi T, 2001, SYNLETT, P879
[9]   Rhodium-catalyzed asymmetric addition of organo-boron and -titanium reagents to electron-deficient olefins [J].
Hayashi, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2004, 77 (01) :13-21
[10]   Enolate generation under hydrogenation conditions: Catalytic Aldol cycloreduction of keto-enones [J].
Huddleston, RR ;
Krische, MJ .
ORGANIC LETTERS, 2003, 5 (07) :1143-1146