A reusable enantioselective catalytic system for the Kharasch-Sosnovsky allylic oxidation of alkenes based on a ditopic azabis(oxazoline) ligand

被引：29

作者：

Aldea, Luis ^{[1
]}

Delso, Ignacio ^{[2
]}

Hager, Markus ^{[3
]}

Glos, Martin ^{[3
]}

Garcia, Jose I. ^{[1
]}

Mayoral, Jose A. ^{[1
,4
]}

Reiser, Oliver ^{[3
]}

机构：

[1] Univ Zaragoza, CSIC, Inst Sintesis Quim & Catalisis Homogenea, Dept Organ Chem, E-50009 Zaragoza, Spain

[2] Univ Zaragoza, CSIC, Ctr Quim & Mat Aragon, NMR Serv, E-50009 Zaragoza, Spain

[3] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

[4] Univ Zaragoza, Inst Univ Catalisis Homogenea, E-50009 Zaragoza, Spain

来源：

TETRAHEDRON | 2012年 / 68卷 / 17期

关键词：

Copper catalysis; Bis(oxazoline) ligands; Allylic oxidation; Kharasch-Sosnovsky oxidation; Supported catalysts; OXAZOLINE-CONTAINING LIGANDS; FLUOROUS BIS(OXAZOLINES); COORDINATION POLYMERS; COPPER(I) COMPLEXES; SPECTROSCOPY DOSY; CHIRAL CATALYSTS; DIFFUSION; OLEFINS; NMR; IMMOBILIZATION;

D O I：

10.1016/j.tet.2011.10.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easily recoverable and reusable enantioselective catalytic system based on the self-assembly of a coordination polymer through the use of a chiral ditopic ligand, is described for the allylic oxidation of cycloalkenes with tert-butyl perbenzoate. Upon addition of the substrates and a coordinating solvent (acetone or acetonitrile) the coordination polymer disassembles, allowing the catalysis to take place in homogeneous phase. After completion of the reaction, the catalyst reassembles as a coordination polymer upon solvent evaporation and addition of hexane, and is recovered as an insoluble solid. This way, good enantioselectivities and yields are obtained in seven consecutive operation cycles. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3417 / 3422

页数：6

共 67 条

[1] Discrimination of metallosupramolecular architectures in solution by using diffusion ordered spectroscopy (DOSY) experiments: Double-stranded helicates of different lengths [J].