5,10,15-tris(o-aminophenyl) corrole (TAPC) as a versatile synthon for the preparation of corrole-based hemoprotein analogs.

[structure: see text] The atropisomers of 5,10,15-tris(o-aminophenyl) corrole (alphabetaalpha, alphaalphabeta, and alphaalphaalpha) are metastable at room temperature as a result of the low rotational barrier of the o-aminophenyl pickets adjacent to the bipyrrole moiety. Atropisomer enrichment of TAPC was required for the preparation of picket fence, triazacyclononane-capped, and trisimidazole-alphaalphaalpha-corroles. A racemic alpha(2)beta model of cis-A(2)B geometry was also obtained by linking two cis anilines with a short strap and inserting an imidazole tail on the opposite face of TAPC.