Stereoselective synthesis of [2.2]triphenylenophanes via intramolecular double [2 + 2 + 2] cycloadditions.

ABSTRACT: Planar chiral [2.2]cyclophanes with two aromatic rings in close proximity have attracted much attention for their applications as chiral materials and catalysts because of their stable chirality and transannular interactions. Although numerous [2.2]cyclophanes have been synthesized to date, only a few polycyclic aromatic hydrocarbon (PAH)-based ones have been reported, and the simultaneous control of two planar chiralities of the two aromatic rings facing each other has not been achieved. Here we report the enantio- and/or diastereoselective synthesis of planar chiral PAH-based [2.2]cyclophanes ([2.2]triphenylenophanes) via the high-yielding base-mediated intermolecular macrocyclization and Rh- or Ni-catalyzed intramolecular double [2 + 2 + 2] cycloadditions. DFT calculations have r

SUBMITTER: Kawai Y 

PROVIDER: S-EPMC10094470 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature