Enantiomerically Pure P,N Chelates Based on Phospholene Rings: Palladium Complexes and Catalytic Applications in Allylic Substitution

被引：14
|
作者：
Leca, Francois [1 ]
Fernandez, Fernando [2 ]
Muller, Guillermo [2 ]
Lescop, Christophe [1 ]
Reau, Regis [1 ]
Gomez, Montserrat [2 ,3 ]
机构：
[1] Univ Rennes 1, UMR Sci Chim Rennes 6226, F-35042 Rennes, France
[2] Univ Barcelona, Dept Quim Inorgan, E-08028 Barcelona, Spain
[3] Univ Toulouse 3, Lab Heterochim Fondamentale & Appl, CNRS, UMR 5069, F-31120 Toulouse 9, France
来源：
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2009年 / 36期
关键词：
Palladium; Asymmetric catalysis; Chiral resolution; P ligands; Allylic substitutions; (PHOSPHANYLOXAZOLINE)PALLADIUM COMPLEXES; NMR INVESTIGATIONS; CHIRAL PHOSPHINES; COORDINATION; LIGANDS; ALKYLATION; VERSATILE; BEHAVIOR;
D O I：
10.1002/ejic.200900892
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The synthesis of optically Pure 2-pyridylphospholene ligands by diastereomeric resolution of Pd-II complexes, bearing the corresponding racemic P,N ligand and (R)-alpha-methylbenzylamine, by means of fractional crystallisation is described. A full coordination study of palladium complexes containing 2-pyridylphospholene and the corresponding phosphole ligands, both in solution (by means of NMR spectroscopy) and in the solid state (by X-ray diffraction), was carried out, These ligands were evaluated in Pd-catalysed allylic substitution of racemic substrates (rac-3-acetoxy-1,3-diphenyl-1-propene and rac-3-acetoxy-1-cyclohexene) and (E)-3-acetoxy-1-phenyl-1-propene. A modelling study of the palladium allylic intermediates was performed in order to justify the asymmetric induction observed with the 2-pyridylphospholene ligands. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码：5583 / 5591
页数：9
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