An efficient Cu(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase catalyst for asymmetric carbon-carbon bond formation

被引：37

作者：

Doherty, Simon ^{[1
]}

Knight, Julian G. ^{[1
]}

Ellison, Jack R. ^{[1
]}

Goodrich, Peter ^{[2
]}

Hall, Leanne ^{[2
]}

Hardacre, Christopher ^{[2
]}

Muldoon, Mark J. ^{[2
]}

Park, Soomin ^{[2
]}

Ribeiro, Ana ^{[3
,4
]}

Nieto de Castro, Carlos Alberto ^{[3
,4
]}

Lourenco, Maria Jose ^{[3
,4
]}

Davey, Paul ^{[5
]}

机构：

[1] Newcastle Univ, Sch Chem, NUCAT, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

[2] Queens Univ Belfast, Sch Chem & Chem Engn, QUILL Res Ctr, Belfast BT9 5AG, Antrim, North Ireland

[3] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal

[4] Univ Lisbon, Fac Ciencias, Ctr Ciencias Mol & Mat, P-1749016 Lisbon, Portugal

[5] Givaudan, Schweiz AG, CH-8600 Dubendorf, Switzerland

来源：

GREEN CHEMISTRY | 2014年 / 16卷 / 03期

关键词：

ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS; MUKAIYAMA ALDOL REACTION; DIELS-ALDER REACTION; CHIRAL CATALYSTS; BIS(OXAZOLINE)-COPPER COMPLEXES; HETEROGENEOUS CATALYST; METAL-COMPLEXES; CYCLOPENTADIENE;

D O I：

10.1039/c3gc41378k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric Diels-Alder reaction between N-acryloyloxazolidinone and cyclopentadiene and the Mukaiyama-aldol reaction between methylpyruvate and 1-phenyl-1-trimethylsilyloxyethene have been catalysed by heterogeneous copper(II)-bis(oxazoline)-based polymer immobilised ionic liquid phase (PIILP) systems generated from a range of linear and cross linked ionic polymers. In both reactions selectivity and ee were strongly influenced by the choice of polymer. A comparison of the performance of a range of Cu(II)-bis(oxazoline)-PIILP catalyst systems against analogous supported ionic liquid phase (SILP) heterogeneous catalysts as well as their homogeneous counterparts has been undertaken and their relative merits evaluated.

引用

页码：1470 / 1479

页数：10

共 38 条

[1] Polymer-supported chloroaluminate catalysts for the Diels-Alder reaction of cyclopentadiene with methyl methacrylate [J].