Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly. Issue 33 (8th September 2017)

• Record Type: Journal Article
• Authors: Struch, Niklas; Frömbgen, Christopher; Schnakenburg, Gregor; Lützen, Arne
• Is Part Of: European journal of organic chemistry. Issue 33(2017)
• Page Start: 4984
• Page End: 4989
• Publication Date: 2017-09-08
• Subjects: Self‐assembly -- Iron -- Supramolecular chemistry -- Helical structures -- Self‐sorting; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700921
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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 Fe2 L3 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. Abstract : Homochiral helicates are 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. Self‐assembly occurs through a diastereoselective and narcissistic self‐sorting manner to form Fe2 L3 helicates. The stereochemistry of the metal centres is directed by the axial chirality of the BINOL‐based backbone.