Synthesis, Chiral Resolution, and Absolute Configuration of <i>C</i>₂‐Symmetric, Chiral 9,9′‐Spirobifluorenes

Abstract

Abstract Racemic 2,2′‐, 2,2′,7,7′‐, and 2,2′,3,3′‐substituted 9,9′‐spirobifluorenes were synthesised and successfully resolved by HPLC on a Chiralpak IA stationary phase on both analytical and semipreparative scales. Their absolute configurations were determined by comparison of their specific optical rotations with literature data or by comparison of retention times with independently prepared enantiopure material. These compounds are versatile C 2 ‐symmetric building blocks for the formation of more sophisticated cleft‐like, chiral molecular architectures.