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
[1]   A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
ORGANIC LETTERS, 2001, 3 (23) :3781-3784
[2]   Stereoselectivity in ring-closing olefin metathesis (RCM) of tethered dihexenoyl derivatives [J].
Arisawa, M ;
Kaneko, H ;
Nishida, A ;
Nakagawa, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (07) :959-964
[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]  
Arisawa M, 1997, SYNLETT, P1179
[5]  
Arisawa M, 2000, CHEM PHARM BULL, V48, P1593
[6]   Concise synthesis of azacycloundecenes using ring-closing metathesis (RCM) [J].
Arisawa, M ;
Kato, C ;
Kaneko, H ;
Nishida, A ;
Nakagawa, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1873-1876
[7]  
Arisawa M, 2000, SYNLETT, P841
[8]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[9]   Olefin isomerization by a ruthenium carbenoid complex. Cleavage of allyl and homoallyl groups [J].
Cadot, C ;
Dalko, PI ;
Cossy, J .
TETRAHEDRON LETTERS, 2002, 43 (10) :1839-1841
[10]   Synthesis of functionalized olefins by cross and ring-closing metatheses [J].
Chatterjee, AK ;
Morgan, JP ;
Scholl, M ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (15) :3783-3784