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.
Collman
James P
JP
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. jpc@stanford.edu
Decréau
Richard A
RA
D006420:Hemeproteins / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006420:Hemeproteins; D006576:Heterocyclic Compounds, 4 or More Rings; D011166:Porphyrins; C431863:corrole