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Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration

Author:
Varghese, Shaji, Spierenburg, Bram, Swartjes, Anne, White, Paul B., Tinnemans, Paul, Elemans, Johannes A. A. W., Nolte, Roeland J. M.
Source:
Organic letters 2018 v.20 no.13 pp. 3719-3722
ISSN:
1523-7052
Subject:
X-ray diffraction, chemical reactions, chemical structure, chromatography, materials, porphyrins, receptors, regioselectivity
Abstract:
Nitration of tetraphenylporphyrin cage compound 1, at −40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at −30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography.
Agid:
6083970