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Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly
Author(s) -
Struch Niklas,
Frömbgen Christopher,
Schnakenburg Gregor,
Lützen Arne
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700921
Subject(s) - chemistry , chirality (physics) , stereochemistry , ligand (biochemistry) , self assembly , nuclear magnetic resonance spectroscopy , enantiomer , enantioselective synthesis , spectroscopy , crystallography , catalysis , organic chemistry , receptor , biochemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Homochiral helicates were prepared through subcomponent self‐assembly with a C 2 ‐symmetric chiral building block based on a 6,6′‐substituted 1,1′‐bi‐2‐naphthol (BINOL) scaffold. The resulting complexes were analysed through a broad variety of NMR spectroscopy experiments, high‐resolution mass spectrometry, CD and UV/Vis spectroscopy, and single‐crystal X‐ray diffraction. As proven by these experiments, the self‐assembly occurs through a completely diastereoselective and narcissistic self‐sorting manner to form homochiral Fe 2 L 3 helicates. The stereochemistry of the metal centres is directed by the axial chirality of the BINOL‐based backbone; the ( M )‐configured ligand forms the (Δ,Δ) complex, and the ( P )‐configured ligand forms the (Λ,Λ) complex.