Construction of Heterocycles by the Strategic Use of Alkyne π-Activation in Catalyzed Cascade Reactions

被引：256
作者：
Kirsch, Stefan F. [1 ]
机构：
[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany
来源：
SYNTHESIS-STUTTGART | 2008年 / 20期
关键词：
cascade reactions; catalysis; gold; platinum; heterocycles;
D O I：
10.1055/s-0028-1083164
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This review highlights the synthesis of heterocycles via cascade reactions that involve the activation of an alkyne using carbophilic Lewis acids. Primarily guided by the type of reactivity evolving from the alkyne activation, such key steps are categorized as the addition of simple heteroatom nucleophiles, intramolecular carboalkoxylations, addition of carbonyl nucleophiles, rearrangement of propargylic esters, and enyne cycloisomerizations. Additionally, the functionalization of existing heterocycles is discussed.
引用
收藏
页码：3183 / 3204
页数：22
相关论文
共 287 条
[1]   Sequential amination/annulation/aromatization reaction of carbonyl compounds and propargylamine: A new one-pot approach to functionalized pyridines [J].
Abbiati, G ;
Arcadi, A ;
Bianchi, G ;
Di Giuseppe, S ;
Marinelli, F ;
Rossi, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6959-6966
[2]   Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].
Alfonsi, M ;
Arcadi, A ;
Aschi, M ;
Bianchi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273
[3]   Gold(I)-catalysed arylation of 1,6-enynes: different site reactivity of cyclopropyl gold carbenes [J].
Amijs, Catelijne H. M. ;
Ferrer, Catalina ;
Echavarren, Antonio M. .
CHEMICAL COMMUNICATIONS, 2007, (07) :698-700
[4]   Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].
Antoniotti, S ;
Genin, E ;
Michelet, V ;
Genêt, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977
[5]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[6]   Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles [J].
Arcadi, A ;
Bianchi, G ;
Marinelli, F .
SYNTHESIS-STUTTGART, 2004, (04) :610-618
[7]  
Arcadi A, 2001, ADV SYNTH CATAL, V343, P443, DOI 10.1002/1615-4169(200107)343:5<443::AID-ADSC443>3.3.CO
[8]  
2-R
[9]   Conversion of homochiral amines and α-amino esters to their chiral 1,2,3,5-substituted pyrrole derivatives via gold-catalysed amination/annulation reactions of 2-propynyl-1,3-dicarbonyl compounds [J].
Arcadi, A ;
Di Giuseppe, S ;
Marinelli, F ;
Rossi, E .
TETRAHEDRON-ASYMMETRY, 2001, 12 (19) :2715-2720
[10]   A new green approach to the Friedlander synthesis of quinolines [J].
Arcadi, A ;
Chiarini, M ;
Di Giuseppe, S ;
Marinelli, F .
SYNLETT, 2003, (02) :203-206
12345678910