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Highly Enantioselective Michael Additions of Indole to Benzylidene Malonate Using Simple Bis(oxazoline) Ligands: Importance of Metal/Ligand Ratio
Rasappan, Ramesh, Hager, Markus, Gissibl, Anja and Reiser, Oliver
(2006)
Highly Enantioselective Michael Additions of Indole to Benzylidene Malonate Using Simple Bis(oxazoline) Ligands: Importance of Metal/Ligand Ratio.
Organic Letters 8 (26), pp. 6099-6102.
Date of publication of this fulltext: 05 Aug 2009 13:40
Article
DOI to cite this document: 10.5283/epub.2531
Abstract
Simple bis(oxazoline) ligands, especially azabis(oxazolines), can catalyze the copper-catalyzed addition of indoles to benzylidene malonates in up to > 99% ee, provided that excess of chiral ligand is avoided. The paradigm followed in many asymmetric catalyses that an excess of chiral ligand with respect to the metal should improve enantioselectivity because a background reaction by free metal is ...
Simple bis(oxazoline) ligands, especially azabis(oxazolines), can catalyze the copper-catalyzed addition of indoles to benzylidene malonates in up to > 99% ee, provided that excess of chiral ligand is avoided. The paradigm followed in many asymmetric catalyses that an excess of chiral ligand with respect to the metal should improve enantioselectivity because a background reaction by free metal is suppressed, is not applicable here, which might call for revisiting some of the many copper(II)-bis(oxazoline)-catalyzed processes known.
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| Item type | Article | ||||
| Journal or Publication Title | Organic Letters | ||||
| Publisher: | AMER CHEMICAL SOC | ||||
|---|---|---|---|---|---|
| Place of Publication: | WASHINGTON | ||||
| Volume: | 8 | ||||
| Number of Issue or Book Chapter: | 26 | ||||
| Page Range: | pp. 6099-6102 | ||||
| Date | 2006 | ||||
| Institutions | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser | ||||
| Identification Number |
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| Keywords | FRIEDEL-CRAFTS ALKYLATIONS; ASYMMETRIC CATALYSIS; KINETIC RESOLUTION; COMPLEXES; | ||||
| Dewey Decimal Classification | 600 Technology > 610 Medical sciences Medicine | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| Item ID | 2531 |
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