Enantiomerically pure tetrahydroisoquinolines from the gold-catalysed isomerization of substrates derived from furans and amino acids

被引:33
作者
Hashmi, A. Stephen K. [1 ]
Ata, Filiz [1 ]
Kurpejovic, Elzen [1 ]
Huck, Juergen [1 ]
Rudolph, Matthias [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
关键词
alkynes; amino acids; aziridines; furans; gold;
D O I
10.1007/s11244-007-0297-5
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new route to enantiomerically pure 8-hydroxytetrahydroisoquinolines is based on furan derivatives and amino acids from renewable resources and gold catalysis. The stereogenic centre from the amino acid remains unchanged in the product.
引用
收藏
页码:245 / 251
页数:7
相关论文
共 39 条
[1]   Efficient chemoselective alcohol oxidation using oxygen as oxidant.: Superior performance of gold over palladium catalysts [J].
Abad, Alberto ;
Almela, Carles ;
Corma, Avelino ;
Garcia, Hermenegildo .
TETRAHEDRON, 2006, 62 (28) :6666-6672
[2]   Recent applications of gold catalysis in organic synthesis [J].
Arcadi, A ;
Di Giuseppe, S .
CURRENT ORGANIC CHEMISTRY, 2004, 8 (09) :795-812
[3]  
Bischler A., 1893, CHEM BER-RECL, V26, P1903, DOI [DOI 10.1002/CBER.189302602143, 10.1002/cber.189302602143]
[4]   Heterogeneous gold-catalysed synthesis of phenols [J].
Carrettin, Silvio ;
Blanco, M. Carmen ;
Corma, Avelino ;
Hashmi, A. Stephen K. .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (10-11) :1283-1288
[5]   C-3-symmetric tripodal tetra-amines - preparation from chiral amino alcohols via aziridines [J].
Cernerud, M ;
Adolfsson, H ;
Moberg, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2655-2662
[6]   SYNTHESIS OF AN N2S-CYCLODECANE MACROCYCLE AND ITS NICKEL(II) COMPLEX [J].
CHANDRASEKHAR, S ;
MCAULEY, A .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (20) :2967-2970
[7]   The catalytic activity of "Naked" gold particles [J].
Comotti, M ;
Della Pina, C ;
Matarrese, R ;
Rossi, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (43) :5812-5815
[8]  
Comotti M., 2004, ANGEW CHEM, V116, P5936
[9]  
Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO
[10]  
2-A