Chiral thiazoline ligands: application in Pd-catalysed allylic substitution

被引:63
作者
Abrunhosa, I [1 ]
Delain-Bioton, L [1 ]
Gaumont, AC [1 ]
Gulea, M [1 ]
Masson, S [1 ]
机构
[1] ENSICAEN Univ, CNRS, UMR 6507, Lab Chim Mol & Thioorgan, F-14050 Caen, France
关键词
thiazolines; oxazolines; chiral ligands; asymmetric catalysis; allylic substitution;
D O I
10.1016/j.tet.2004.07.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of thiazoline ligands, analogues of well-known oxazolines, easily prepared from chiral aminoalcohols, and appropriate dithioesters, was tested in the Pd-catalysed allylic substitution. A systematic comparison with the corresponding oxazolines (using literature data or our own tests) has been made for each case. Some important differences (between their catalytic activity and enantioselectivity) were noted for the two types of ligands, especially in the case of bis(thiazolines) and bis(oxazolines). (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9263 / 9272
页数:10
相关论文
共 41 条
[1]   Efficient new protocol to synthesize aromatic and heteroaromatic dithioesters [J].
Abrunhosa, I ;
Gulea, M ;
Masson, S .
SYNTHESIS-STUTTGART, 2004, (06) :928-934
[2]   Synthesis of new chiral thiazoline-containing ligands [J].
Abrunhosa, I ;
Gulea, M ;
Levillain, J ;
Masson, S .
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2851-2859
[3]  
ABRUNHOSA I, 2003, THESIS CAEN U
[4]   PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS [J].
ALLEN, JV ;
COOTE, SJ ;
DAWSON, GJ ;
FROST, CG ;
MARTIN, CJ ;
WILLIAMS, JMJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15) :2065-2072
[5]  
Braunstein P, 2001, ANGEW CHEM INT EDIT, V40, P680, DOI 10.1002/1521-3773(20010216)40:4<680::AID-ANIE6800>3.0.CO
[6]  
2-0
[7]   Steric effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation using chiral oxazolinylpyridines [J].
Chelucci, G ;
Medici, S ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1999, 10 (03) :543-550
[8]   Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines [J].
Chelucci, G ;
Deriu, S ;
Pinna, GA ;
Saba, A ;
Valenti, R .
TETRAHEDRON-ASYMMETRY, 1999, 10 (19) :3803-3809
[9]   Chiral oxazolinylpyridines as ligands for enantioselective palladium catalysed allylic substitution [J].
Chelucci, G ;
Medici, S ;
Saba, A .
TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3183-3184
[10]   Unexpected reversal of the enantioselectivity using chiral quinolylmethyl- and acridininyloxazolines as ligands for asymmetric palladium-catalyzed allylic alkylation [J].
Chelucci, G ;
Pinna, GA ;
Saba, A ;
Valenti, R .
TETRAHEDRON-ASYMMETRY, 2000, 11 (19) :4027-4036