Iron Corrole-catalyzed [4+2] Cycloaddition of Dienes and Aldehydes

被引:27
作者
Kuwano, Toru [1 ]
Kurahashi, Takuya [1 ,2 ]
Matsubara, Seijiro [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan
关键词
DIELS-ALDER REACTIONS; HIGH-VALENT METALLOPORPHYRIN; ELECTRONIC-STRUCTURE; PORPHYRIN; COMPLEXES; REARRANGEMENT; EPOXIDES; CYCLOISOMERIZATION; ROUTES;
D O I
10.1246/cl.130672
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have developed cationic iron(IV) corrole-catalyzed formal hetero-Diels-Alder reaction of aldehydes with dienes, which opens the way for divergent synthesis of pyrans. The potential utility of the catalyst was also demonstrated by carrying out cycloaddition of alpha,beta-unsaturated aldehyde with a diene to give pyran selectively. Furthermore, the catalytic reactivity of iron corrole complex on the cycloaddition was determined by comparing that of iron porphyrin complex.
引用
收藏
页码:1241 / 1243
页数:3
相关论文
共 30 条
[1]   MECHANISTIC INVESTIGATIONS OF PORPHYRIN SYNTHESES .I. PRELIMINARY STUDIES ON MS-TETRAPHENYLPORPHIN [J].
ADLER, AD ;
SHERGALI.W ;
LONGO, FR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) :3145-&
[2]   Trifluoromethanesulfonic acid, an efficient catalyst for the hetero Diels-Alder reaction and an improved synthesis of mefrosol. [J].
Aggarwal, VK ;
Vennall, GP ;
Davey, PN ;
Newman, C .
TETRAHEDRON LETTERS, 1997, 38 (14) :2569-2572
[3]  
[Anonymous], 1987, Hetero Diels Alder methodology in Organic Synthesis
[4]   A practical and mild method for the highly selective conversion of terminal alkenes into aldehydes through epoxidation-isomerization with ruthenium(IV)-porphyrin catalysts [J].
Chen, J ;
Che, CM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (37) :4950-4954
[5]   Cationic Iron(III) Porphyrin-Catalyzed [4+2] Cycloaddition of Unactivated Aldehydes with Simple Dienes [J].
Fujiwara, Kyohei ;
Kurahashi, Takuya ;
Matsubara, Seijiro .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (12) :5512-5515
[6]   Electronic structure of gallium, copper, and nickel complexes of corrole. High-valent transition metal centers versus noninnocent ligands [J].
Ghosh, A ;
Wondimagegn, T ;
Parusel, ABJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5100-5104
[7]   PRINS REACTIONS OF ARYLALDEHYDES .2. DIENES [J].
GRIENGL, H ;
GEPPERT, KP .
MONATSHEFTE FUR CHEMIE, 1976, 107 (03) :675-684
[8]   REACTIONS OF KETENE ACETALS .15. REGIOSPECIFIC SYNTHESES OF ERYTHROLACCIN AND 7-HYDROXYERYTHROLACCIN [J].
GUAY, V ;
BRASSARD, P .
TETRAHEDRON, 1984, 40 (24) :5039-5045
[9]   Scandium(III) perfluorooctanesulfonate [Sc(OPf)(3)]: A novel catalyst for the hetero Diels-Alder reaction of aldehydes with non-activated dienes [J].
Hanamoto, T ;
Sugimoto, Y ;
Jin, TZ ;
Inanaga, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (06) :1421-1426
[10]   Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones [J].
Huang, Y ;
Rawal, VH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) :9662-9663