Asymmetric systematic synthesis, structures, and (chir)optical properties of a series of dihetero[8]helicenes.

ABSTRACT: A series of dihetero[8]helicenes have been systematically synthesized in enantiomerically enriched forms by utilizing the characteristic transformations of the organosulfur functionality. The synthetic route begins with assembling a ternaphthyl common synthetic intermediate from 2-naphthol and bissulfinylnaphthalene through an extended Pummerer reaction followed by facile multi-gram-scale resolution. The subsequent cyclization reactions into dioxa- and dithia[8]helicenes take place with excellent axial-to-helical chirality conversion. Dithia[8]helicene is further transformed into the nitrogen and the carbon analogs by replacing the two endocyclic sulfur atoms via S_NAr-based skeletal reconstruction. The efficient systematic synthesis has enabled comprehensive evaluation of

SUBMITTER: Yanagi T 

PROVIDER: S-EPMC8179410 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature