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Fraile, José M. ; Pérez, Ignacio ; Mayoral, José A. ; Reiser, Oliver

Multipurpose box- and azabox-Based Immobilized Chiral Catalysts

Fraile, José M. , Pérez, Ignacio, Mayoral, José A. and Reiser, Oliver (2006) Multipurpose box- and azabox-Based Immobilized Chiral Catalysts. Advanced Synthesis & Catalysis 348 (12-13), pp. 1680-1688.

Date of publication of this fulltext: 05 Aug 2009 13:40
Article
DOI to cite this document: 10.5283/epub.2528


Abstract

Azabis(oxazolines) can be used as chiral ligands in the copper-catalyzed enantioselective Mukaiyama aldol reaction. When supported on solids, azabis(oxazoline)-copper complexes are more easily deactivated than their analogous bis(oxazoline)copper complexes, and are not compatible with the use of coordinating solvents in the method of preparation. The performance of the immobilized catalysts (up ...

Azabis(oxazolines) can be used as chiral ligands in the copper-catalyzed enantioselective Mukaiyama aldol reaction. When supported on solids, azabis(oxazoline)-copper complexes are more easily deactivated than their analogous bis(oxazoline)copper complexes, and are not compatible with the use of coordinating solvents in the method of preparation. The performance of the immobilized catalysts (up to 86 % ee) depends on the support and the reaction solvent, with some positive effect on enantioselectivity due to surface effects. The deactivation is not irreversible and the deactivated catalysts show excellent performance in the cyclopropanation reaction, providing added value to the supported multipurpose catalysts.



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Details

Item typeArticle
Journal or Publication TitleAdvanced Synthesis & Catalysis
Publisher:WILEY-V C H VERLAG GMBH
Place of Publication:WEINHEIM
Volume:348
Number of Issue or Book Chapter:12-13
Page Range:pp. 1680-1688
DateAugust 2006
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number
ValueType
10.1002/adsc.200606121DOI
KeywordsENANTIOSELECTIVE ALDOL ADDITIONS; SUPPORTED BIS(OXAZOLINE)-COPPER COMPLEXES; C(2)-SYMMETRIC COPPER(II) COMPLEXES; POLYMER-BOUND BIS(OXAZOLINE); OXAZOLINE-CONTAINING LIGANDS; DIELS-ALDER REACTIONS; CYCLOPROPANATION REACTIONS; ASYMMETRIC HYDROGENATION; ELECTROSTATIC INTERACTIONS; LEWIS-ACIDS; asymmetric catalysis; azabis(oxazolines); cyclopropanation; Mukaiyama aldol; supported catalysts
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgUnknown
Item ID2528

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