Synthesis of Chiral Thiazoline Ligands Tethered to a Sulfur Function and First Immobilization of a Thiazoline-Ligand

被引:10
作者
Abrunhosa-Thomas, Isabelle [1 ]
Betz, Alexander [1 ]
Denance, Mickael [1 ]
Dez, Isabelle [1 ]
Gaumont, Annie-Claude [1 ]
Gulea, Mihaela [1 ]
机构
[1] Univ Caen Basse Normandie, CNRS, ENSICAEN, Lab Chim Mol & Thioorgan,INC3M,FR 3038,UMR 6507, F-14050 Caen, France
关键词
ASYMMETRIC ALLYLIC SUBSTITUTION; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE CATALYSIS; BIS(OXAZOLINE) LIGANDS; BIS(THIAZOLINE); OXAZOLINES; PALLADIUM; EFFICIENT; DITHIOESTERS; SUPPORTS;
D O I
10.1002/hc.20603
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new family of thiazoline ligands tethered to a sulfanyl or a sulfinyl group has been prepared using short and efficient reaction sequences. Among the different structures, one sulfanyl-thiazoline homopolymer was synthesized as a first example of an immobilized thiazoline ligand. The catalytic properties of these new ligands were evaluated in the Pd-catalyzed allylic substitution. (C) 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:242-249, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20603
引用
收藏
页码:242 / 249
页数:8
相关论文
共 35 条
[1]   Chiral thiazoline ligands: application in Pd-catalysed allylic substitution [J].
Abrunhosa, I ;
Delain-Bioton, L ;
Gaumont, AC ;
Gulea, M ;
Masson, S .
TETRAHEDRON, 2004, 60 (41) :9263-9272
[2]   Efficient new protocol to synthesize aromatic and heteroaromatic dithioesters [J].
Abrunhosa, I ;
Gulea, M ;
Masson, S .
SYNTHESIS-STUTTGART, 2004, (06) :928-934
[3]   Synthesis of new chiral thiazoline-containing ligands [J].
Abrunhosa, I ;
Gulea, M ;
Levillain, J ;
Masson, S .
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2851-2859
[4]   PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS [J].
ALLEN, JV ;
DAWSON, GJ ;
FROST, CG ;
WILLIAMS, JMJ ;
COOTE, SJ .
TETRAHEDRON, 1994, 50 (03) :799-808
[5]   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
[6]   ENANTIOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION - ELECTRONIC AND STERIC EFFECTS OF THE LIGAND [J].
ALLEN, JV ;
BOWER, JF ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1994, 5 (10) :1895-1898
[7]   Hydroxyalkyl Thiazolines, a New Class of Highly Efficient Ligands for Carbonyl Additions [J].
Bauer, Michael ;
Maurer, Erattke ;
Hoffmann, Svenja M. ;
Kazmaier, Uli .
SYNLETT, 2008, (20) :3203-3207
[8]  
BAYON JC, 2003, COORDIN CHEM REV, V242, P159
[9]   Using Soluble Polymer Supports To Facilitate Homogeneous Catalysis [J].
Bergbreiter, David E. ;
Tian, Jianhua ;
Hongfa, Chayanant .
CHEMICAL REVIEWS, 2009, 109 (02) :530-582
[10]   Using soluble polymers to recover catalysts and ligands [J].
Bergbreiter, DE .
CHEMICAL REVIEWS, 2002, 102 (10) :3345-3383