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2-Dihydromethylpiperazinediium-M(II) (M(II) = Cu(II), Fe(II), Co(II), Zn(II)) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction.
MedLine Citation:
PMID:  23059799     Owner:  NLM     Status:  Publisher    
A series of double dihydromethylpiperazinediium metallic sulfates [H(2)mpz]M(II)(SO(4))(2)·nH(2)O (mpz = 2-methylpiperazine, C(5)H(12)N(2)) are prepared by slow evaporation using a racemic (R/S)-mpz (for , ) or enantiopure R-mpz (for ), S-mpz (for ) and sulfates of Cu(II) (for ), Fe(II) (for , ), Co(II) (for ) and Zn(II) (for , , ), and characterized by infrared spectroscopy, elemental analysis and single crystal X-ray diffraction. The [M(II)(H(2)O)(6)](2+), [(R/S)-H(2)mpz](2+), [(R)-H(2)mpz](2+) or [(S)-H(2)mpz](2+) cations and 2SO(4)(2-) anions are linked together via two types of hydrogen bonds, Ow-HwO and N-HO, 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 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.
Houcine Naïli; Fadhel Hajlaoui; Tahar Mhiri; Tatiana C O Mac Leod; Maximilian N Kopylovich; Kamran T Mahmudov; Armando J L Pombeiro
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-10-11
Journal Detail:
Title:  Dalton transactions (Cambridge, England : 2003)     Volume:  -     ISSN:  1477-9234     ISO Abbreviation:  Dalton Trans     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-10-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101176026     Medline TA:  Dalton Trans     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Laboratoire de l'Etat Solide, Département de Chimie, Université de Sfax, BP 1171, 3000 Sfax, Tunisie.
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