5,10,15-Tris(o-aminophenyl) Corrole (TAPC) as a Versatile Synthon for the Preparation of Corrole-Based Hemoprotein Analogs

Org. Lett., 7 (6), 975 -978, 2005. 10.1021/ol048185s S1523-7060(04)08185-4
Web Release Date: February 23, 2005

5,10,15-Tris(o-aminophenyl) Corrole (TAPC) as a Versatile Synthon for the Preparation of Corrole-Based Hemoprotein Analogs

James P. Collman* and Richard A. Decréau

Department of Chemistry, Stanford University, Stanford, California 94305-5080

jpc@stanford.edu

Received September 8, 2004

Abstract:

The atropisomers of 5,10,15-tris(o-aminophenyl) corrole (

, and

) 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-

-corroles. A racemic

₂

model of cis-A₂B geometry was also obtained by linking two cis anilines with a short strap and inserting an imidazole tail on the opposite face of TAPC.

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