Erbium(III) triflate: A valuable catalyst for the synthesis of aldimines, ketimines, and enaminones

被引:61
作者
Dalpozzo, R
De Nino, A
Nardi, M
Russo, B
Procopio, A
机构
[1] Univ Calabria, Dipartimento Chim, I-87030 Arcavacata Di Rende, Cs, Italy
[2] Magna Graecia Univ Catanzaro, Dipartimento Sci Farmacobiol, I-88021 Roccelletta Di Borgia, Cz, Italy
来源
SYNTHESIS-STUTTGART | 2006年 / 07期
关键词
imines; enaminones; erbium triflate; Lewis acids; catalysis;
D O I
10.1055/s-2006-926378
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldimines, ketimines, and enaminones can be obtained under erbium(III) triflate catalysis. The reaction mechanism is that typical of imine synthesis. The role of the catalyst is demonstrated for the synthesis of aromatic imines. In contrast to CeCl3/NaI addition to unsaturated aldehydes, which results in Michael addition, no Michael adduct was observed under erbium(III) triflate catalysis.
引用
收藏
页码:1127 / 1132
页数:6
相关论文
共 57 条
[1]   Photorearrangement of N-alkanoyl beta-enaminones. Application to the synthesis of alpha-amino-beta,gamma-unsaturated acid derivatives [J].
Amougay, A ;
Letsch, O ;
Pete, JP ;
Piva, O .
TETRAHEDRON, 1996, 52 (07) :2405-2420
[2]   Gold catalysis in the reactions of 1,3-dicarbonyls with nucleophiles [J].
Arcadi, A ;
Bianchi, G ;
Di Giuseppe, S ;
Marinelli, F .
GREEN CHEMISTRY, 2003, 5 (01) :64-67
[3]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[4]  
2-E
[5]   A novel synthesis of disubstituted ureas using titanium(IV) isopropoxide and sodium borohydride [J].
Armstrong, JD ;
Wolfe, CN ;
Keller, JL ;
Lynch, J ;
Bhupathy, M ;
Volante, RP ;
DeVita, RJ .
TETRAHEDRON LETTERS, 1997, 38 (09) :1531-1532
[6]   Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid [J].
Aspinall, HC ;
Bissett, JS ;
Greeves, N ;
Levin, D .
TETRAHEDRON LETTERS, 2002, 43 (02) :323-325
[7]  
BARALDI PG, 1983, SYNTHESIS-STUTTGART, P902
[8]   Improved heteroatom nucleophilic addition to electron-poor alkenes promoted by CeCl3•7H2O/NaI system supported on alumina in solvent-free conditions [J].
Bartoli, G ;
Bartolacci, M ;
Giuliani, A ;
Marcantoni, E ;
Massaccesi, M ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :169-174
[9]   Zn(ClO4)2•6H2O as a powerful catalyst for the conversion of β-ketoesters into β-enamino esters [J].
Bartoli, G ;
Bosco, M ;
Locatelli, M ;
Marcantoni, E ;
Melchiorre, P ;
Sambri, L .
SYNLETT, 2004, (02) :239-242
[10]  
BARTOLI G, 1990, SYNTHESIS-STUTTGART, P895