Olefin cross-metathesis for the synthesis of heteroaromatic compounds

被引:55
作者
Donohoe, Timothy J. [1 ]
Bower, John F. [1 ]
Chan, Louis K. M. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
基金
英国工程与自然科学研究理事会;
关键词
RING-CLOSING METATHESIS; POLYSUBSTITUTED FURANS; PYRROLES; CONSTRUCTION; (R)-(+)-MUSCOPYRIDINE; FUNCTIONALIZATION; HETEROCYCLES; SEQUENCES; CHLORIDES; EFFICIENT;
D O I
10.1039/c2ob06659a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The olefin metathesis reaction has underpinned spectacular achievements in organic synthesis in recent years. Arguably, metathesis has now become the foremost choice for a carbon-carbon double bond disconnection. Despite this general utility, de novo routes to heteroaromatic compounds using the cross-metathesis (CM) reaction have only recently emerged as an efficient strategy. This approach allows a convergent union of simple, functionalised, three- to four-carbon olefinic core building blocks, to generate furans, pyrroles and pyridines with a high degree of control of substitution pattern in the product.
引用
收藏
页码:1322 / 1328
页数:7
相关论文
共 51 条
[1]   Two Titanium-Catalyzed Reaction Sequences for Syntheses of Pyrroles from (E/Z)-Chloroenynes or α-Haloalkynols [J].
Ackermann, Lutz ;
Sandmann, Rene ;
Kaspar, Ludwig T. .
ORGANIC LETTERS, 2009, 11 (09) :2031-2034
[2]   NOVEL CONVERSION OF EPOXIDES TO ONE-CARBON HOMOLOGATED ALLYLIC ALCOHOLS BY DIMETHYLSULFONIUM METHYLIDE [J].
ALCARAZ, L ;
HARNETT, JJ ;
MIOSKOWSKI, C ;
MARTEL, JP ;
LEGALL, T ;
SHIN, DS ;
FALCK, JR .
TETRAHEDRON LETTERS, 1994, 35 (30) :5449-5452
[3]   Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene-ene metathesis and ene-enol ether metathesis [J].
Arisawa, M ;
Theeraladanon, C ;
Nishida, A ;
Nakagawa, M .
TETRAHEDRON LETTERS, 2001, 42 (45) :8029-8033
[4]   Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes [J].
Barluenga, Jose ;
Riesgo, Lorena ;
Vicente, Ruben ;
Lopez, Luis A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13528-+
[5]   Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives [J].
Benakki, Hafid ;
Colacino, Evelina ;
Andre, Christophe ;
Guenoun, Farhate ;
Martinez, Jean ;
Lamaty, Frederic .
TETRAHEDRON, 2008, 64 (25) :5949-5955
[6]  
Bonnet V, 2002, SYNLETT, P1008
[7]   A general model for selectivity in olefin cross metathesis [J].
Chatterjee, AK ;
Choi, TL ;
Sanders, DP ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (37) :11360-11370
[8]   Counterion Effects in a Gold-Catalyzed Synthesis of Pyrroles from Alkynyl Aziridines [J].
Davies, Paul W. ;
Martin, Nicolas .
ORGANIC LETTERS, 2009, 11 (11) :2293-2296
[9]   Coupling-isomerization-enamine addition-cyclocondensation sequences:: A multicomponent approach to substituted and annelated pyridines [J].
Dediu, OG ;
Yehia, NAM ;
Oeser, T ;
Polborn, K ;
Müeller, TJJ .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (09) :1834-1848
[10]   Synthesis of (-)-(Z)-deoxypukalide [J].
Donohoe, Timothy J. ;
Ironmonger, Alan ;
Kershaw, Neil M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (38) :7314-7316