2026-10-14T16:50:17Z https://www.scidb.cn/oai

10.11922/sciencedb.o00049.00004 2022-01-06T11:08:27Z

2022-01-06 Raw Data for the article "Development of novel C2-symmetrical [5]oxahelicenoid diols" doi:10.11922/sciencedb.o00049.00004 en we synthesized a new C2-symmetric [5]oxahelicenoid diol 14 from [5]oxahelicenoid dione 13 by either DDQ mediated or Pd/C catalyzed dehydrogenative aromatization. Optical resolution of (rac)-14 with N-benzylquininium chloride 15 and N-benzylquinidinium chloride 16 afforded the enantiomerically pure (P)-14 and (M)-14, respectively. In addition, six chiral phosphoric acids 19a~19f were synthesized from (P)-14 and subjected to an enantioselective Friedel-Crafts reaction to afford the desired product 22 in good results (up to 94% yield, 76:24 er). The result indicates that the catalysts based on our newly synthesized [5]oxahelicenoid diol have comparable catalytic activity as BINOL-based and SPINOL-based ones. Chiral diols; Helical chirality; Chiral phosphoric acids; Enantioselective Friedel-Crafts reaction Guodong Sun Jiancun Zhang PUBLIC https://creativecommons.org/licenses/by/4.0/ dataset http://www.doi.org/10.1016/j.tetlet.2021.153026 Science Data Bank