Open AccessGoldberg Active Template Synthesis of a [2]Rotaxane Ligand for Asymmetric Transition-Metal Catalysis
Author(s) -
Steven Hoekman,
Matthew O. Kitching,
David A. Leigh,
Marcus Papmeyer,
Diederik Roke
Publication year - 2015
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.5b04726
Subject(s) - rotaxane , chemistry , ligand (biochemistry) , catalysis , enantioselective synthesis , conjugate , combinatorial chemistry , stereochemistry , transition metal , supramolecular chemistry , molecule , organic chemistry , receptor , mathematical analysis , biochemistry , mathematics
We report on the active template synthesis of a [2]rotaxane through a Goldberg copper-catalyzed C-N bond forming reaction. A C2-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.