Novel concepts in directed biaryl synthesis, XXXIV. Synthesis, optical resolution, and helimerization of dinaphtho[2,1‐<i>b</i>:1′,2′‐<i>d</i>]‐pyran‐4‐one

Abstract

Abstract A rational synthesis of the biaryl lactone 3 is described. This bridged biaryl, which gradually helimerizes at room temperature, could be synthesized in a non‐racemic form, chemically by atropo‐selective ring opening with a chiral O ‐nucleophile and subsequent ring closure, and chromatographically by HPLC on a chiral phase. For the enantiomerization process ( M )‐ 3 ⇄ ( P )‐ 3 , the activation parameters were determined. magnified image