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Rasappan, Ramesh ; Hager, Markus ; Gissibl, Anja ; Reiser, Oliver

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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Details

Item typeArticle
Journal or Publication TitleOrganic Letters
Publisher:AMER CHEMICAL SOC
Place of Publication:WASHINGTON
Volume:8
Number of Issue or Book Chapter:26
Page Range:pp. 6099-6102
Date2006
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
Identification Number
ValueType
10.1021/ol062697kDOI
KeywordsFRIEDEL-CRAFTS ALKYLATIONS; ASYMMETRIC CATALYSIS; KINETIC RESOLUTION; COMPLEXES;
Dewey Decimal Classification600 Technology > 610 Medical sciences Medicine
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
Item ID2531

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