Novel three-component reactions based on a Heck carbopalladation/cyclization domino reaction

被引:39
作者
Kressierer, CJ [1 ]
Müller, TJJ [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
amination; C-C coupling; domino reactions; multicomponent reactions; olefination;
D O I
10.1002/anie.200461134
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In one fell swoop: the reaction of alkynyl-allyl alcohols with aryl halides in the presence of [Pd(PPh3)2Cl2] under Heck reaction conditions provides cyclic γ,δ-enals (see scheme). This reaction serves as the starting sequence for the one-pot synthesis of diene esters and β-amino-substituted tetrahydrofurans.
引用
收藏
页码:5997 / 6000
页数:4
相关论文
共 36 条
[1]   Pd-assisted multicomponent synthesis of heterocycles [J].
Balme, G ;
Bossharth, E ;
Monteiro, N .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111
[2]  
Battistuzzi G, 2002, EUR J ORG CHEM, V2002, P2671
[3]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[4]  
2-A
[5]  
Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99
[6]   A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence [J].
Braun, RU ;
Zeitler, K ;
Muller, TJJ .
ORGANIC LETTERS, 2001, 3 (21) :3297-3300
[7]   PALLADIUM CATALYZED [2+2+2]-CYCLOADDITION REACTIONS VIA CARBOPALLADATION OF 1,6-ENYNES [J].
BROWN, S ;
CLARKSON, S ;
GRIGG, R ;
SRIDHARAN, V .
TETRAHEDRON LETTERS, 1993, 34 (01) :157-160
[8]  
BUNTIN SA, 1990, ORG SYNTH COLL, V7, P361
[9]   PALLADIUM-CATALYZED REACTION OF VINYLIC HALIDES WITH PRIMARY ALLYLIC ALCOHOLS - REGIO AND STEREOCONTROLLED SYNTHESIS OF 4-ENALS [J].
JEFFERY, T .
TETRAHEDRON LETTERS, 1990, 31 (46) :6641-6644
[10]   A novel one-pot four-component access to tetrahydro-β-carbolines by a coupling-amination-aza-annulation-Pictet-Spengler sequence (CAAPS) [J].
Karpov, AS ;
Oeser, T ;
Müller, TJJ .
CHEMICAL COMMUNICATIONS, 2004, (13) :1502-1503