Goldberg Active Template Synthesis of a [2]Rotaxane Ligand for Asymmetric Transition-Metal Catalysis

We report on the active template synthesis of a [2]­rotaxane through a Goldberg copper-catalyzed C–N bond forming reaction. A C 2-symmetric cyclohexyldiamine macrocycle directs the assembly of the rotaxane, which can subsequently serve as a ligand for enantioselective nickel-catalyzed conjugate addi...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-06, Vol.137 (24), p.7656-7659
Main Authors: Hoekman, Steven, Kitching, Matthew O, Leigh, David A, Papmeyer, Marcus, Roke, Diederik
Format: Article
Language:English
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Summary:We report on the active template synthesis of a [2]­rotaxane through a Goldberg copper-catalyzed C–N bond forming reaction. A C 2-symmetric cyclohexyldiamine macrocycle directs the assembly of the rotaxane, which can subsequently serve as a ligand for enantioselective nickel-catalyzed conjugate addition reactions. Rotaxanes are a previously unexplored ligand architecture for asymmetric catalysis. We find that the rotaxane gives improved enantioselectivity compared to a noninterlocked ligand, at the expense of longer reaction times.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b04726