Abstract
Synthesis of unsymmetrical [7]-helical compounds possessing the dispiro[2,1-c]indenofluorene motif was achieved for the first time in good yields. The crucial step of the whole reaction sequence was catalytic intramolecular [2 + 2 + 2] cycloaddition of triynediols by using various transition metal compounds (Co, Ni, etc.). The cyclotrimerizations were accompanied by dehydro-Diels-Alder reaction giving rise to other types of aromatic compounds depending on the respective reaction conditions. Limits of enantioselective cyclotrimerization were assessed. The subsequent transformations of the cyclotrimerization products provided the respective dispiroindenofluorenes. Structures of both unsymmetrical [7]helical cyclotrimerization products as well as three dehydro-Diels-Alder products were unequivocally confirmed by single-crystal X-ray diffraction analyses. Photophysical properties of selected products were determined as well.
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