Planar‐Chiral [2.2]Paracyclophane‐Based Amides as Proligands for Titanium‐ and Zirconium‐Catalyzed Hydroamination

A synthetic route to racemic and enantiopure planar chiral [2.2]paracyclophanes with amide groups was developed to combine the well‐established reactivity of amides as N,O‐chelating ligands in hydroamination reactions with the planar chirality of the [2.2]paracyclophane backbone. A mono‐ as well as...

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Veröffentlicht in:European journal of organic chemistry 2017-04, Vol.2017 (13), p.1760-1764
Hauptverfasser: Braun, Carolin, Bräse, Stefan, Schafer, Laurel L.
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Sprache:eng
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Zusammenfassung:A synthetic route to racemic and enantiopure planar chiral [2.2]paracyclophanes with amide groups was developed to combine the well‐established reactivity of amides as N,O‐chelating ligands in hydroamination reactions with the planar chirality of the [2.2]paracyclophane backbone. A mono‐ as well as a tethered bis(amide) were synthesized and investigated as ligands for titanium and zirconium. Hydroamination reactivity studies showed their ability to translate their planar chirality into central chirality in the product. A synthetic route to racemic and enantiopure planar chiral [2.2]paracyclophanes with amide groups was developed for use as N,O‐chelating ligands in hydroamination reactions. When coordinated to titanium or zirconium, hydroamination reactivity studies showed that the planar chirality of the ligand was translated into central chirality in the product.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700101