Crystal structure of a chiral binaphthyl porphyrin

Abstract

Condensation of tetrakis-5,10,15,20-(α,β,α,β-2-aminophenyl)porphyrin atropoisomer with 1,1′-binaphthyl, 2,2′-dimethoxy-3,3′-diacetylchloride afforded the corresponding basket handle porphyrin whose structure has been analyzed by X-ray crystallography. The macrocycle presents a ruffled type plane according to Shelnutt method for classifying and quantifying the out-of-plane and in-plane distortion of a porphyrin. This structure clearly shows the position of the methoxy groups with respect to the center of the porphyrin and their possible role in the enantioselective epoxidation and cyclopropanation of olefins.