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
相关论文
共 35 条
[11]   Rh(I)-catalyzed carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids leading to indenones [J].
Harada, Yasuyuki ;
Nakanishi, Jun ;
Fujihara, Hirokazu ;
Tobisu, Mamoru ;
Fukumoto, Yoshiya ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (17) :5766-5771
[12]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[13]   Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].
Hayashi, T ;
Yamasaki, K .
CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844
[14]   Oxindole synthesis through intramolecular nucleophilic addition of vinylpalladiums to aryl isocyanates [J].
Kamijo, S ;
Sasaki, Y ;
Kanazawa, C ;
Schüsseler, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7718-7721
[15]   A convenient synthesis of (E)-α-alkylidene-γ-lactams and (E)-3-alkylideneoxindoles by rhodium-catalyzed intramolecular hydroamidation [J].
Kobayashi, Y ;
Kamisaki, H ;
Yanada, K ;
Yanada, R ;
Takemoto, Y .
TETRAHEDRON LETTERS, 2005, 46 (44) :7549-7552
[16]   Addition of organostannanes to isocyanate catalyzed by a rhodium complex [J].
Koike, T ;
Takahashi, M ;
Arai, N ;
Mori, A .
CHEMISTRY LETTERS, 2004, 33 (10) :1364-1365
[17]   Intermolecular rhodium-catalyzed carbometalation/Heck-type reaction in water [J].
Kurahashi, Takuya ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (38) :6336-6338
[18]   Regioselective rhodium-catalyzed addition of arylboronic acids to alkynes with a pyridine-substituted water-soluble ligand [J].
Lautens, M ;
Yoshida, M .
ORGANIC LETTERS, 2002, 4 (01) :123-125
[19]   Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR [J].
Lin, SN ;
Yang, ZQ ;
Kwok, BHB ;
Koldobskiy, M ;
Crews, CM ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (20) :6347-6355
[20]   Formation of carbocycles through sequential carborhodation triggered by addition of organoborons [J].
Miura, Tomoya ;
Murakami, Masahiro .
CHEMICAL COMMUNICATIONS, 2007, (03) :217-224