The ionic liquid ethyltri-n-butylphosphonium tosylate as solvent for the acid-catalysed hetero-Michael reaction

被引:32
作者
Karodia, Nazira [1 ]
Liu, Xihan [1 ]
Ludley, Petra [1 ]
Pletsas, Dirnitrios [1 ]
Stevenson, Grace [1 ]
机构
[1] Univ Bradford, Sch Life Sci, Bradford BD7 1DP, W Yorkshire, England
关键词
D O I
10.1016/j.tet.2006.09.052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and convenient method for the acid-catalysed Michael addition reactions of alcohols, thiols and amines to methyl vinyl ketone has been developed using the ionic liquid ethyltri-n-butylphosphonium tosylate. The reaction conditions are mild and obviate the need for toxic and expensive Lewis acid catalysts, offering advantages over more commonly used systems. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:11039 / 11043
页数:5
相关论文
共 53 条
[1]   Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].
Alam, MM ;
Varala, R ;
Adapa, SR .
TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119
[2]  
Anastas P. T., 1998, GREEN CHEM THEORY PR
[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]   Highly diastereoselective conjugate addition of lithium dialkylamides to alpha,beta-unsaturated esters having a chiral center at the gamma-position [J].
Asao, N ;
Shimada, T ;
Sudo, T ;
Tsukada, N ;
Yazawa, K ;
Gyoung, YS ;
Uyehara, T ;
Yamamoto, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6274-6282
[6]   Sequential one-pot InBr3-catalyzed 1,4-then 1,2-nucleophilic addition to enones [J].
Bandini, M ;
Cozzi, PG ;
Giacomini, M ;
Melchiorre, P ;
Selva, S ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3700-3704
[7]   Synthesis of anticancer β-lactams:: mechanism of action [J].
Banik, BK ;
Becker, FF ;
Banik, I .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (10) :2523-2528
[8]   Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].
Bartoli, G ;
Bosco, M ;
Marcantoni, E ;
Petrini, M ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055
[9]   A new class of selective myocardial calcium channel modulators. 2. Role of the acetal chain in oxadiazol-3-one derivatives [J].
Budriesi, R ;
Carosati, E ;
Chiarini, A ;
Cosimelli, B ;
Cruciani, G ;
Ioan, P ;
Spinelli, D ;
Spisani, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2445-2456
[10]  
Bull SD, 2000, SYNLETT, P1257