[9,9′]Bi[naphtho(2,1-b)furanyl]-8,8′-diol, a furo-fused BINOL derivative: synthesis, resolution and determination of absolute configuration

Crystal structures of Mosher's salt and ester elucidated by X-ray crystallography

“…The structures of alcohol moieties may have affected the crystal conformations of the MTPA moieties. In addition, the intramolecular interactions (e.g., the C-H … p interaction and the C-H … O hydrogen bond) were often observed between the acyl and alcohol moieties in the crystalline MTPA esters in which the ester-carbonyl and trifluoromethyl groups were not syn (e.g., CCDC 282786 45 and CCDC 723548 46 ). Also, note that irregular conformations were frequently observed in the bis-or tris-MTPA esters (e.g., CCDC 292039 47 and CCDC 734060 48 ).…”

Sterically Congested Chiral 7,8‐Dioxa[6]helicene and Its Dihydro Analogues: Synthesis, Regioselective Functionalization, and Unexpected Domino Prins Reaction

“…The NMR spectroscopic data are complementary to the results obtained from HPLC on a chiral stationary phase and X‐ray analysis. The 1 H NMR spectra of 8a – c show a downfield shift in the signals of the protons attached to the C1 and C14 carbon atoms in the range of δ = 8.0–9.2 ppm relative to the signal of the proton attached to the C1 carbon atom of naphtha[2,1‐ b ]furan‐8‐ol, which appears at δ = 7.15 ppm 14. This downfield shift in the signals establishes the close proximity of these hydrogen atoms, which are influenced by the magnetic anisotropy effect of the other terminal ring.…”

Furo-Fused BINOL Based Crown as a Fluorescent Chiral Sensor for Enantioselective Recognition of Phenylethylamine and Ethyl Ester of Valine

“…Recently, a furo-fused BINOL derivative was developed in our laboratory. This molecule, ( R )-(−)[9,9‘]bi[naphtho(2,1- b )furanyl]-8,8‘-diol ( 1 ) (Figure ), presented a potentially promising chiral scaffold for the construction of a suitable chiral crown host for possible enantioselective complexation with chiral ammmonium guests. Molecule 1 has many desired features such as C 2 symmetry, a sufficiently enlarged dihedral angle for better stereo-discrimination, and modified electronic properties as compared to BINOL.…”