Ru-catalyzed tandem cross-metathesis/intramolecular-hydroarylation sequence

被引:115
作者
Chen, Jia-Rong [1 ]
Li, Chang-Feng [1 ]
An, Xiao-Lei [1 ]
Zhang, Ji-Ji [1 ]
Zhu, Xiao-Yu [1 ]
Xiao, Wen-Jing [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China
关键词
cross-metathesis; homogeneous catalysis; hydroarylation; ruthenium; tandem reactions;
D O I
10.1002/anie.200705194
中图分类号
O6 [化学];
学科分类号
0703 [化学];
摘要
(Chemical Equation Presented) Sometimes it only takes one to tango: A novel ruthenium-catalyzed tandem cross-metathesis/intramolecular-hydroarylation reaction of alkenyl indoles has been developed which relies on a single catalyst for the tandem sequence and provides an efficient synthesis of fused polycyclic indole compounds with good to excellent overall yields (see scheme; Ts = 4-toluenesulfonyl, DCE = 1,2-dichloroethane, Mes = 2,4,6-Me3C 6H2). © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2489 / 2492
页数:4
相关论文
共 58 条
[1]
New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 [J].
Agnusdei, M ;
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7126-7129
[2]
Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations [J].
Ajamian, A ;
Gleason, JL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3754-3760
[3]
Ajamian A., 2004, ANGEW CHEM, V116, P3842
[4]
A practical synthetic route to functionalized THBCs and oxygenated analogues via intramolecular Friedel-Crafts reactions [J].
Angeli, Marco ;
Bandini, Marco ;
Garelli, Andrea ;
Piccinelli, Fabio ;
Tommasi, Simona ;
Umani-Ronchi, Achille .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) :3291-3296
[5]
The metathesis reactions: from a historical perspective to recent developments [J].
Astruc, D .
NEW JOURNAL OF CHEMISTRY, 2005, 29 (01) :42-56
[6]
Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation [J].
Bandini, M ;
Melloni, A ;
Piccinelli, F ;
Sinisi, R ;
Tommasi, S ;
Umani-Ronchi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1424-1425
[7]
Sequential catalysis: A metathesis/dihydroxylation sequence [J].
Beligny, S ;
Eibauer, S ;
Maechling, S ;
Blechert, S .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (12) :1900-1903
[8]
Beligny S., 2006, N HETEROCYCLIC CARBE, P1
[9]
Bentz D, 2000, SYNTHESIS-STUTTGART, P1766
[10]
Synthesis of strychnine [J].
Bonjoch, J ;
Solé, D .
CHEMICAL REVIEWS, 2000, 100 (09) :3455-3482