Merging Synthesis and Enantioselective Functionalization of Indoles by a Gold-Catalyzed Asymmetric Cascade Reaction

被引：65
作者：
Chiarucci, Michel [2 ]
Mocci, Rita [1 ]
Syntrivanis, Leonidas-Dimitrios [1 ]
Cera, Gianpiero [1 ]
Mazzanti, Andrea [2 ]
Bandini, Marco [1 ]
机构：
[1] Alma Mater Studiorum Univ Bologna, Dept Chem G Ciamician, I-40126 Bologna, Italy
[2] Alma Mater Studiorum Univ Bologna, Dept Ind Chem Toso Montanari, I-40136 Bologna, Italy
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 41期
关键词：
allylic alkylation; asymmetric catalysis; cascade reaction; gold; indoles; ALLYLIC ALKYLATION; ALCOHOLS; EFFICIENT; CYCLIZATION; ACTIVATION;
D O I：
10.1002/anie.201304619
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
All at once: The simultaneous synthesis and enantioselective functionalization of an indole core is achieved with the assistance of chiral cationic AuI complexes. A range of vinyloxazino-[4,3-a]indoles is obtained by a cascade process in a highly enantioselective manner (see scheme; L=chiral diphosphine). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：10850 / 10853
页数：4
相关论文
共 78 条
[1]  
Adcock H. V., 2012, SYNTHESIS-STUTTGART, P3401
[2]   Gold-catalyzed reactions of 2-alkynyl-phenylamines with α,β-enones [J].
Alfonsi, M ;
Arcadi, A ;
Aschi, M ;
Bianchi, G ;
Marinelli, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06) :2265-2273
[3]   Efficient and general synthesis of oxazino[4,3-a]indoles by cascade addition-cyclization reactions of (1H-indol-2-yl)methanols and vinyl sulfonium salts [J].
An, Jing ;
Chang, Ning-Jie ;
Song, Li-Dong ;
Jin, Yu-Qin ;
Ma, Ying ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2011, 47 (06) :1869-1871
[4]  
[Anonymous], 2011, ANGEW CHEM
[5]  
[Anonymous], 2010, ANGEW CHEM INT EDIT, DOI [DOI 10.1002/ANGE.20, DOI 10.1002/ANGE.200905341]
[6]  
[Anonymous], 2012, ANGEW CHEM
[7]  
Bandini M., 2009, Catalytic Asymmetric Friedel-Crafts Alkylations
[8]  
Bandini M., 2009, Angew. Chem. Int. Ed, V121, P9697
[9]  
Bandini M., 2009, ANGEW CHEM, V121, P9786, DOI DOI 10.1002/ange.200901843
[10]  
Bandini M., 2012, SYNTHESIS, P504
12345678