Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions

被引:97
作者
Gilbertson, SR [1 ]
Hoge, GS [1 ]
机构
[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(98)00265-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium catalyst is reported that catalyzes the cycloisomerization of dieneynes and trienes. This cycloisomerization reaction, formally the equivalent of an unactivated Diels-Alder reaction, proceeds at room temperature with [Rh(DIPHOS)(CH2Cl2)(2)] SbF6 as the catalyst. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2075 / 2078
页数:4
相关论文
共 16 条
[1]   Asymmetric catalytic intramolecular hydroacylation of 4-substituted pent-4-enals to beta-substituted cyclopentanones [J].
Barnhart, RW ;
McMorran, DA ;
Bosnich, B .
CHEMICAL COMMUNICATIONS, 1997, (06) :589-590
[2]  
BUCHHOLZ H, 1972, COORDIN CHEM REV, V8, P129
[3]   OLIGOMERIZATION CATALYSTS .3. CYCLOCODIMERIZATION OF CONJUGATED DIENES WITH ACETYLENIC HYDROCARBONS CATALYZED BY IRON(O) COMPLEXES . SYNTHESIS OF 1,2-DIPHENYL-1,4-CYCLOHEXADIENE [J].
CARBONARO, A ;
GRECO, A ;
DALLASTA, G .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10) :3948-+
[4]   Chiral rhodium complexes as catalysts in Diels-Alder reactions [J].
Carmona, D ;
Cativiela, C ;
GarciaCorreas, R ;
Lahoz, FJ ;
Lamata, MP ;
Lopez, JA ;
deViu, MPLR ;
Oro, LA ;
SanJose, E ;
Viguri, F .
CHEMICAL COMMUNICATIONS, 1996, (10) :1247-1248
[5]  
DAVIS R, 1975, CHEM COMMUN, P405
[6]  
DIECK HT, 1983, ANGEW CHEM INT EDIT, V22, P778
[7]  
GENET JP, 1979, TETRAHEDRON LETT, P1499
[8]   NOVEL CYCLIZATION REACTIONS ON TRANSITION-METAL TEMPLATES - THE CATALYSIS OF INTRAMOLECULAR [4 + 2] CYCLOADDITIONS BY LOW VALENT RHODIUM COMPLEXES [J].
JOLLY, RS ;
LUEDTKE, G ;
SHEEHAN, D ;
LIVINGHOUSE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (12) :4965-4966
[9]   Transition metal-mediated cycloaddition reactions [J].
Lautens, M ;
Klute, W ;
Tam, W .
CHEMICAL REVIEWS, 1996, 96 (01) :49-92
[10]   CYCLO-CODIMERIZATION OF 1,3-BUTADIENE DERIVATIVES WITH NONACTIVATED TERMINAL ACETYLENES CATALYZED BY CATIONIC RHODIUM(I) COMPLEX [J].
MATSUDA, I ;
SHIBATA, M ;
SATO, S ;
IZUMI, Y .
TETRAHEDRON LETTERS, 1987, 28 (29) :3361-3362