The synthesis of optically active calix[4]arenes with one or three substituents on the methylene bridgesElectronic supplementary information (ESI) available: Experimental procedures and characterization of all new compounds including X-ray data for (S)-12. CCDC 785086. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c0cc02689a

A facile synthesis of optically active mono and trisubstituted calix[4]arenes is described wherein the chirality at the methylene bridges arises from centers of chirality present in the diyne and the bis-carbene complex from which they are constructed. Optically active calix[4]arenas can be directly accessed from the triple annulation of chiral bis-carbene complexes and chiral diynes.