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A stereodynamic phosphoramidite ligand derived from 3,3'-functionalized ortho-biphenol and its rhodium(I) complex

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Stereodynamic ligands and complexes bearing functional groups to attach chiral or achiral binding sites and auxiliaries are highly attractive due to the interesting opportunities for controlling the stereochemical outcome of enantioselective transformations. In this study we report the preparation o...

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Bibliographic Details
Main Authors: Storch, Golo (Author) , Menke, Jan-Michael (Author) , Rominger, Frank (Author) , Trapp, Oliver (Author)
Format: Article (Journal)
Language:English
Published: 28 October 2016
In: Chirality
Year: 2016, Volume: 28, Issue: 11, Pages: 744-748
ISSN:1520-636X
DOI:10.1002/chir.22655
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chir.22655
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chir.22655
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Author Notes:Golo Storch, Luisa Deberle, Jan-Michael Menke, Frank Rominger, Oliver Trapp
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Summary:Stereodynamic ligands and complexes bearing functional groups to attach chiral or achiral binding sites and auxiliaries are highly attractive due to the interesting opportunities for controlling the stereochemical outcome of enantioselective transformations. In this study we report the preparation of a 3,3′-functionalized biphenol (BIPOL) phosphoramidite ligand (PAm) bearing 3,5-dichlorobenzoyl (3,5-DCB) amide binding sites for noncovalent interactions. Upon coordination to [Rh(COD)2]BF4 this substitution pattern directs one of the 3,5-DCB binding sites in close proximity of the metal center resulting in liberation of both COD ligands and the formation of a [Rh(PAm)2]BF4 complex. Coordination of the amide carbonyl unit was found to be reversible, since the complex acted as an active catalyst in the hydrogenation of dehydroamino acid derivatives. X-ray crystallographic investigation revealed that the second 3,5-DCB unit is capable of forming noncovalent π-π interactions connecting both phosphoramidite ligands.
Item Description:Gesehen am 15.05.2020
Physical Description:Online Resource
ISSN:1520-636X
DOI:10.1002/chir.22655

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