Abstract
Chiral methanocyclooctadiindoles, featuring an indole-annulated bicyclo[3.3.1]nonane framework, were obtained from the corresponding bicyclo[3.3.1]nonane 2,6-, 2,7- and 3,7-diketones via the Fischer indolization reaction. The chiroptical properties of the cleft-like conformationally rigid derivatives, exhibiting a well-defined spatial arrangement of the two indole chromophores, were studied by means of electronic circular dichroism (CD) spectroscopy and time-dependent density functional theory (TDDFT) calculations. The absolute configuration of 7,14-methanocyclooctadiindole derived from an achiral bicyclic 3,7-diketone was established using the exciton chirality method and corroborated by TDDFT calculations.
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