The axially dissymmetric pyrrole as a novel chiral building block: synthesis, characterization and application to the first ‘predetermined’ synthesis of a chiral atropisomeric porphyrin with molecular asymmetry

Abstract

The first axially dissymmetric pyrroles, 4-methyl-3-(2′-methoxy-1′-naphthyl)pyrrole-2-carboxylates 1, were synthesized, characterized by X-ray crystallography and circular dichroism analysis, and applied to the first ‘predetermined’ synthesis of a chiral atropisomeric porphyrin with molecular asymmetry, (R,R,R,R)- and (S,S,S,S)- 2,7,12,17-tetramethyl-3,8,13,18-tetrakis(2′-methoxy-1′-naphthyl)porphyrin