A chiral iridium complex catalyzed a consecutive and enantioselective [2+2+2] cycloaddition of polyynes to give axially chiral compounds. Intermolecular reaction of tetraynes, possessing aryl groups on their termini, with protected but-2-yne-1,4-diols gave C2-symmetrical quateraryl compounds. Intramolecular reaction of hexaynes, possessing aryl or alkyl groups on their termini gave C2-symmetrical biaryl compounds. The catalytic synthesis of a pentacene derivative with axial chiralities is also discussed.
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