Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis

被引:180
作者
Arisawa, M [1 ]
Terada, Y [1 ]
Nakagawa, M [1 ]
Nishida, A [1 ]
机构
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan
关键词
D O I
10.1002/anie.200290031
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aruthenium complex, generated from the Grubbs carbene catalyst with vinyloxytrimethylsilane, catalyzed the isomerization of terminal alkenes RCH2-CH=CH2 to internal alkenes RCH=CH-CH3. Application of this olefin isomerization to 2-(N-allylamino)styrene gave the corresponding enamines, which were converted into indoles by a standard ring-closing metathesis, see scheme (Ts = tosyl).
引用
收藏
页码:4732 / 4734
页数:3
相关论文
共 38 条
[21]  
HOULIHAN WJ, 1972, CHEM HETEROCYCLIC CO
[22]   An unexpected product arising from metal alkylidene mediated ring-closing diene metathesis [J].
Joe, D ;
Overman, LE .
TETRAHEDRON LETTERS, 1997, 38 (50) :8635-8638
[23]   NICKEL-PROMOTED ISOMERIZATIONS OF ALKENES BEARING POLAR FUNCTIONAL-GROUPS [J].
LOCHOW, CF ;
MILLER, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (18) :3020-3022
[24]   Metathesis of electron-rich olefins: Structure and reactivity of electron-rich carbene complexes [J].
Louie, J ;
Grubbs, RH .
ORGANOMETALLICS, 2002, 21 (11) :2153-2164
[25]   REGIOCONTROLLED SYNTHESIS OF ALLYLSILANES BY MEANS OF RHODIUM(I) OR IRIDIUM(I) CATALYZED ISOMERIZATION OF OLEFINS [J].
MATSUDA, I ;
KATO, T ;
SATO, S ;
IZUMI, Y .
TETRAHEDRON LETTERS, 1986, 27 (47) :5747-5750
[26]   New approaches to total synthesis of manzamine A, ircinal A and related compounds [J].
Nakagawa, M ;
Torisawa, Y ;
Uchida, H ;
Nishida, A .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1999, 57 (11) :1004-1015
[27]   A stereoselective isomerization of allyl silyl ethers to (E)- or (Z)-silyl enol ethers using cationic iridium complexes [J].
Ohmura, T ;
Shirai, Y ;
Yamamoto, Y ;
Miyaura, N .
CHEMICAL COMMUNICATIONS, 1998, (13) :1337-1338
[28]   Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands [J].
Scholl, M ;
Ding, S ;
Lee, CW ;
Grubbs, RH .
ORGANIC LETTERS, 1999, 1 (06) :953-956
[29]   Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligands [J].
Scholl, M ;
Trnka, TM ;
Morgan, JP ;
Grubbs, RH .
TETRAHEDRON LETTERS, 1999, 40 (12) :2247-2250
[30]  
Schuster M, 1997, ANGEW CHEM INT EDIT, V36, P2037