•New class of bisphenol type compounds were synthesized.•Advantages of this work were excellent yields and mild reaction condition.•Stereochemistry was confirmed by single crystal X-ray diffraction method.•The products can be applied as chiral ligands.A new class of helical shaped bi-phenol (1,1′-bibenzo[c]phenanthrene-2,2′-diol; HEBPOL) type derivatives 2a–g were synthesized from quinone derivatives using the conventional 5% Pd-C catalytic reduction process. We obtained excellent yields for all of the 2a–g derivatives. The HEBPOLs were characterized by different analytical techniques including FTIR, 1H NMR, 13C NMR, MS and X-ray crystallography.Download high-res image (82KB)Download full-size image

•Highly optically pure helical quinones were synthesized.•Mild reaction conditions and easy to execute.•Absolute configuration was confirmed by X-ray crystallography.•Optically pure bisphenols are excellent candidate for asymmetric catalysis.Diastereomeric resolution of helically distorted polycondensed bisphenols (1,1′-bibenzo[c]phenanthrene-2,2′-diols: HEBPOLs) 2a–b was conducted utilizing (1R)-(−)-menthyl chloroformate as a chiral resolving agent. Subsequent manipulation produced highly optically pure [>99% enantiomeric excess (ee)] quinone derivatives (P) and (M)-1a–b in very good yields. The absolute configuration of each product was confirmed based on circular dichroism (CD) spectra and X-ray crystal structure analysis.Download high-res image (112KB)Download full-size image

•Short synthetic route of chloro-substituted oxa[9]helicene derivatives.•Synthesized bromo-substituted oxa[9]helicene derivative.•New synthetic approach for unique dibromo spiro-lactone.A new class of halogenated oxa[9]helicene derivatives along with dibromo spiro-lactone were synthesized in excellent yields, and the compounds were successfully characterized by different spectroscopic techniques (e.g. 1H and 13C NMR, HRMS spectroscopy and X-ray crystallography).

The asymmetric coupling reaction of 2-hydroxybenzo[c]phenanthrenes by using Cu–chiral diamine under atmospheric air is described. The use of CuCl-(–)-sparteine and CuCl-cyclohexanediamine derivatives was found to be highly effective to give the helical quinone derivatives in a good yield with high percent enantiomeric excess.

The reaction of helical quinone with alcohols in the presence of Brønsted acid such as para-toluenesulfonic acid (pTSA) or HCl proceeded smoothly to produce the corresponding alkoxy substituted oxa[9]helicenes in good yields.

New oxa[9]helicenes which possess one furan ring have been readily prepared by reactive helical quinone with Lawesson’s reagent or phosphorus pentasulfide in good yields. The versatility of this protocol has been demonstrated with various substituted helical quinones.

•Easy way to synthesis of novel amphiphilic oxa[9]helicenes.•Using chiral column effectively separated the isomers with high optical purity.•Stereochemistry was confirmed by CD spectra analysis.•Optical properties were also investigated.A new class of amphiphilic oxa[9]helicene derivatives were synthesized in excellent-to-fair yields, and successfully characterized by different analytical techniques (e.g., FT-IR, 1H and 13C NMR, and HRMS). The compounds were enantiomerically separated by chiral HPLC and the absolute configurations of the enantiomers were confirmed by circular dichroism spectroscopy. Other optical properties (e.g., UV, photoluminescence, specific optical rotation and molecular optical rotation) of the newly synthesized compounds were also examined.