Synthesis of functionalized resorcinols by rhodium-catalyzed [5+1] cycloaddition reaction of 3-acyloxy-1,4-enynes with CO

被引:56
作者
Brancour, Celia [2 ]
Fukuyama, Takahide [1 ]
Ohta, Yuko [1 ]
Ryu, Ilhyong [1 ]
Dhimane, Anne-Lise [2 ]
Fensterbank, Louis [2 ]
Malacria, Max [2 ]
机构
[1] Osaka Prefecture Univ, Grad Sch Sci, Dept Chem, Osaka 5998531, Japan
[2] Univ Paris 06, Inst Parisien Chim Mol, UMR CNRS 7201, FR 2769, F-75005 Paris, France
关键词
KETENE LIGAND; COMPLEXES; CARBONYLATION; CYCLIZATION; ACETATES; CYCLOISOMERIZATION; 2-CYCLOPENTENONES; N-ENYNES; CHEMISTRY; EFFICIENT;
D O I
10.1039/c0cc00747a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel [5+1] type carbonylative cycloaddition reaction has been developed using a Rh complex as catalyst. This reaction can convert readily available 3-acyloxy-1,4-enynes and CO to a wide range of functionalized resorcinols in good yields. A mechanism involving Rh-catalyzed cyclocarbonylation of 3-acyloxy-1,4-enynes accompanied by a 1,2-acyloxy shift is proposed for the present [5+1] type cycloaddition reaction.
引用
收藏
页码:5470 / 5472
页数:3
相关论文
共 41 条
[1]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[2]   Efficient and general synthesis of 5-(alkoxycarbonyl)methylene-3-oxazolines by palladium-catalyzed oxidative carbonylation of prop-2-ynylamides [J].
Bacchi, A ;
Costa, M ;
Gabriele, B ;
Pelizzi, G ;
Salerno, G .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4450-4457
[3]   Diastereoselective intermolecular rhodium-catalyzed [4+2+2] carbocyclization reactions: Computational and experimental evidence for the intermediacy of an alternative metallacycle intermediate [J].
Baik, MH ;
Baum, EW ;
Burland, MC ;
Evans, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) :1602-1603
[4]   Silicon-initiated carbonylative carbotricyclization and [2+2+2+1] cycloaddition of enediynes catalyzed by rhodium complexes [J].
Bennacer, B ;
Fujiwara, M ;
Lee, SY ;
Ojima, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (50) :17756-17767
[5]   FORMATION OF A STABLE (ETA-2-C,C) KETENE COMPOUND (C5H5)FE(CO)2(CH2CO)+PF6- BY CARBONYLATION OF AN IRON METHYLIDENE COMPLEX - A NOVEL ENTRY INTO CO-DERIVED C-2 CHEMISTRY [J].
BODNAR, TW ;
CUTLER, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (18) :5926-5928
[6]   Dramatic effects of ionic liquids on the palladium-catalyzed cyclocarbonylation of enynols with thiols [J].
Cao, Hong ;
Xiao, Wen-Jing ;
Alper, Howard .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8562-8564
[7]   The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions [J].
Croatt, Mitchell P. ;
Wender, Paul A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (01) :19-32
[8]   Annulation reactions of chromium carbene complexes:: scope, selectivity and recent developments [J].
Dötz, KH ;
Tomuschat, P .
CHEMICAL SOCIETY REVIEWS, 1999, 28 (03) :187-198
[9]  
Evans PA, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P1, DOI 10.1002/3527604693
[10]  
Fukuyama T., E EROS ENCY REAGENTS, DOI DOI 10.1002/047084289X.RC013.PUB2