Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 22, Pages 6470-6474Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201801325
Keywords
bowl-shaped arenes; Cahn-lngold-Prelog system; chirality; circular dichroism spectroscopy; indenocorannulenes
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Chiral corannulenes abound, but suffer generally from configurational lability associated with bowl-to-bowl inversion,([1]) thus obviating questions of stereogenicity and stereoelement construction.([2]) In contrast, peri-annulated corannulenes show greatly increased barriers for bowl-to-bowl inversion; specifically indenocorannulenes invert on a time scale too slow to observe by normal NMR methods and raise the possibility of creating chiral atropisomeric bowl-shaped aromatics.([3]) Two methods for preparing indenocorannulene from simple 2-haloarylcorannulenes-silyl cation C-F activation,([4]) and Pd-mediated C-Cl activation([5])-enable the synthesis of an array of such chiral atropisomeric indeno-corannulenes.([6]) Resolution of the enantiomers by high-performance liquid chromatography over chiral support phases motivates the study of chiroptical properties, the assignment of absolute Cartesian configuration, and the assessment of configurational stability.([7]) These studies bring into question any systematic assignment of nontrivial stereoelements (i.e. not the molecule in its entirety) and refute any assertion of congruence between Cahn-Ingold-Prelog elements and the physical or Cartesian basis of chirality.
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