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Issue 2, 2013
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2-Dihydromethylpiperazinediium-MII (MII = CuII, FeII, CoII, ZnII) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

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Abstract

A series of double dihydromethylpiperazinediium metallic sulfates 1–7 [H2mpz]MII(SO4)2·nH2O (mpz = 2-methylpiperazine, C5H12N2) are prepared by slow evaporation using a racemic (R/S)-mpz (for 1, 2) or enantiopure R-mpz (for 3), S-mpz (for 4–7) and sulfates of CuII (for 5), FeII (for 1, 4), CoII (for 7) and ZnII (for 2, 3, 6), and characterized by infrared spectroscopy, elemental analysis and single crystal X-ray diffraction. The [MII(H2O)6]2+, [(R/S)-H2mpz]2+, [(R)-H2mpz]2+ or [(S)-H2mpz]2+ cations and 2SO42− anions are linked together via two types of hydrogen bonds, Ow–Hw⋯O and N–H⋯O, leading to supramolecular arrangements. The use of the racemic 2-mpz provides alternatives in crystallization: a centrosymmetric structure where the enantiomers are related by an appropriate crystallographic symmetry operation or one where the enantiomers occupy the same crystallographic position, generating disorder. Compounds 1–7 act as diastereoselective catalysts for the nitroaldol (Henry) reaction. The diastereoselectivity can be regulated from exclusive threo to exclusive erythro isomer preparation with typical yields of 50–99%, depending on the catalyst and the substrate used.

Graphical abstract: 2-Dihydromethylpiperazinediium-MII (MII = CuII, FeII, CoII, ZnII) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

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Publication details

The article was received on 11 Apr 2012, accepted on 17 Sep 2012 and first published on 19 Sep 2012


Article type: Paper
DOI: 10.1039/C2DT31300F
Citation: Dalton Trans., 2013,42, 399-406
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    2-Dihydromethylpiperazinediium-MII (MII = CuII, FeII, CoII, ZnII) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

    H. Naïli, F. Hajlaoui, T. Mhiri, T. C. O. Mac Leod, M. N. Kopylovich, K. T. Mahmudov and A. J. L. Pombeiro, Dalton Trans., 2013, 42, 399
    DOI: 10.1039/C2DT31300F

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