Stereoselective synthesis 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids

被引:71
作者
Miura, Tomoya [1 ]
Takahashi, Yusuke [1 ]
Murakami, Masahiro [1 ]
机构
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Katsura, Kyoto 6158510, Japan
关键词
D O I
10.1021/ol7024185
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids furnishes 3-alkylideneoxindoles in a stereoselective manner. The reaction allows arrangement of various substituents on the exocyclic double bond and aromatic ring with wide functional tolerance.
引用
收藏
页码:5075 / 5077
页数:3
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共 35 条
[1]   Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones [J].
Andreani, Aldo ;
Burnelli, Silvia ;
Granaiola, Massimiliano ;
Leoni, Alberto ;
Locatelli, Alessandra ;
Morigi, Rita ;
Rambaldi, Mirella ;
Varoli, Lucilla ;
Kunkel, Mark W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) :6922-6924
[2]   Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water [J].
Bhattacharya, S ;
Sengupta, S .
TETRAHEDRON LETTERS, 2004, 45 (47) :8733-8736
[3]   BIOMIMETIC TOTAL SYNTHESIS OF PSEUDOTABERSONINE - A NOVEL OXINDOLE-BASED APPROACH TO CONSTRUCTION OF ASPIDOSPERMA ALKALOIDS [J].
CARROLL, WA ;
GRIECO, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1164-1165
[4]   Diastereo- and enantioselective catalytic carbometallative aldol cycloreduction: Tandem conjugate addition-aldol cyclization [J].
Cauble, DF ;
Gipson, JD ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1110-1111
[5]   RETRACTED: Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes (Retracted Article) [J].
Chen, Yiyun ;
Lee, Chulbom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15598-15599
[6]   A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].
Cheung, WS ;
Patch, RJ ;
Player, MR .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744
[7]   A domino sequence consisting of insertion, coupling, isomerization, and Diels-Alder steps yields highly fluorescent spirocycles [J].
D'Souza, DM ;
Rominger, F ;
Müller, TJJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (01) :153-158
[8]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[9]   Novel synthesis of oxindoles from carbamoyl chlorides via palladium catalysed cyclisation-anion capture [J].
Fielding, MR ;
Grigg, R ;
Urch, CJ .
CHEMICAL COMMUNICATIONS, 2000, (22) :2239-2240
[10]   Efficient synthesis of trisubstituted alkenes in an aqueous-organic system using a versatile and recyclable Rh/m-TPPTC catalyst [J].
Genin, E ;
Michelet, V ;
Genêt, JP .
TETRAHEDRON LETTERS, 2004, 45 (21) :4157-4161