Chiral and Achiral Basket-Handle Porphyrins: Short Synthesis and Stereostructures of These Versatile Building Blocks

Both,
chiral and achiral basket-handle porphyrins were synthesized
via a short, reliable, and efficient route in multigram quantities.
Standard synthetic protocols such as metalation of the macrocycle,
halogenation, and borylation of the porphyrin core or alkyl- and arylation
with lithium organyls were successfully adapted. The planar-chiral
representatives were resolved into their enantiomers, whose absolute
configurations were determined by comparison of experimental CD spectra
with TDCAM-B3LYP calculated ones.