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dc.contributorWichita State University. Department of Chemistryen_US
dc.contributor.authorBurns, Dennis H.en_US
dc.contributor.authorLi, Yue Heen_US
dc.contributor.authorShi, Dong C.en_US
dc.contributor.authorCaldwell, Timothy M.en_US
dc.identifier.citationThe Journal of organic chemistry. 2002 Jun 28; 67(13): 4536-46.en_US
dc.descriptionFull text of this article is not available in SOAR.en_US
dc.description.abstractThe porphodimethene rearrangement methodology reported in this paper provides for a rational, step-by-step synthesis of chlorins from readily available pyrrole precursors. The intermediate porphodimethenes are furnished directly via the '2 + 2' MacDonald condensation, or by the less symmetry-constrained '3 + 1' condensation of a tripyrrane and bis-formyl pyrrole. The synthetic route is short and highly convergent, especially in the case of the '3 + 1' approach, and furnishes chlorins in good to moderate yields. The synthesis is highly regioselective and appears to be based on the ability of the beta-substituent to stabilize excess electron density, with an electron-neutral hydrogen or an electron-withdrawing carbonyl beta-substituent demonstrating the greatest influence on the formation of the pyrroline ring. The synthesis is highly stereoselective when epimerization of the pyrroline ring beta-carbons is possible, furnishing only the trans-reduced sterioisomer. Finally, there is substantial evidence that a fifth, axial ligand is involved in the transposition of peripheral hydrogens during the rearrangement of the pi-system from metalloporphodimethene to metallochlorin.en_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofseriesThe Journal of organic chemistryen_US
dc.relation.ispartofseriesJ. Org. Chem.en_US
dc.titleThe rational synthesis of chlorins via rearrangement of porphodimethenes: influence of beta-substituents on the regioselectivity and stereoselectivity of pyrroline ring formationen_US
dc.coverage.spacialUnited Statesen_US
dc.description.versionpeer revieweden_US
dc.rights.holderCopyright © 2002 American Chemical Societyen_US

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