Synthesis and characterization of some chiral metal-salen complexes bearing a ferrocenophane substituent

Molecules

Volumn 14, Issue 11, 2009, Pages 4312-4325

  Patti, Angela ^a   Pedotti, Sonia ^a   Ballistreri, Francesco Paolo ^b   Sfrazzetto, Giuseppe Trusso ^b  

^a CNR   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

5 ferrocenophane; Chiral salen ligands; Circular dichroism spectra; Metal complexes

Indexed keywords

4 HYDROXYBENZALDEHYDE; 4-HYDROXYBENZALDEHYDE; BENZALDEHYDE DERIVATIVE; DIPHENYLETHYLENEDIAMINE; ETHYLENEDIAMINE DERIVATIVE; FERROCENE; FERROUS ION; N,N' DISALICYLIDENEETHYLENEDIAMINE; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

BENZALDEHYDES; CIRCULAR DICHROISM; ETHYLENEDIAMINES; FERROUS COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 73349090901     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14114312     Document Type: Article

References (45)

1. Cozzi, P. G. Met al.-salen Schiff base complexes in catalysis: Practical aspects. Chem. Soc. Rev. 2004, 33, 410-421.
2. Bailezao, C.; Garcia, H. Chiral salen complexes: An overview to recoverable and reusable homogeneous and heterogeneous catalysts. Chem. Rev. 2006, 106, 3987-4043.
3. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. Enantioselective epoxidation of unfunctionalized olefins catalyzed by (salen) manganese complexes. J. Am. Chem. Soc. 1990, 112, 2801-2803.
4. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. Highly enantioselective epoxidation catalysts derived from 1, 2-diaminocyclohexane. J. Am. Chem. Soc. 1991, 113, 7063-7064.
5. Srinivasan, K.; Michaud, P.; Kochi, J. K. Epoxidation of olefins with cationic (salen) manganese (III) complexes. The modulation of catalytic activity by substituents. J. Am. Chem. Soc. 1986, 108, 2309-2320.
6. Cavallo, L.; Jacobsen, H. Electronic effects in (salen) Mn-based epoxidation catalysts. J. Org. Chem. 2003, 68, 6202-6207.
7. III complexes. Practical synthesis of enantioenriched terminal epoxides and 1, 2-Diols. J. Am. Chem. Soc. 2002, 124, 1307-1315.
8. Oh, C. R.; Choo, D. J.; Shim, W. H.; Lee, D. H.; Roh, E. J.; Lee, S.; Song, C. E. Chiral Co (III) (salen)-catalysed hydrolytic kinetic resolution of racemic epoxides in ionic liquids. Chem. Commun. 2003, 1100-1101.
9. Dioos, B. M. L.; Jacobs, P. A. Microwave-assisted Cr (salen)-catalysed asymmetric ring opening of epoxides. J. Catal. 2005, 235, 428-430.
10. Kim, H. J.; Kim, W.; Lough, A. J.; Kim, B. M.; Chin, J. A cobalt (III)-salen complex with an axial substituent in the diamine backbone: Stereoselective recognition of amino alcohols. J. Am. Chem. Soc. 2005, 127, 16776-16777.
11. Dzygiel, P.; Reeve, T. B.; Piarulli, U.; Krupicka, M.; Tvaroska, I.; Gennari, C. Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction. Eur. J. Org. Chem. 2008, 1253-1264.
12. Belokon, Y. N.; Fuentes, J., North, M.; Steed, J. W. Influence of the metal and chiral diamine on metal (II) salen catalysed, asymmetric synthesis of α-methyl α-amino acids. Tetrahedron 2004, 60, 3191-3204.
13. Cozzi, P. G. Enantioselective alkynylation of ketones catalyzed by Zn (salen) complexes. Angew. Chem. Int. Ed. 2003, 42, 2895-2898.
14. Pathak, K.; Bhatt, A. P.; Abdi, S. H. R.; Kureshy, R. I.; Khan, N. H.; Ahmad, I.; Jasra, R. Enantioselective phenylacetylene addition to aldehydes and ketones catalyzed by recyclable polymeric Zn (salen) complex. Chirality 2007, 19, 82-88.
15. Wezemberg, S. J.; Kleij, A. W. Material application for salen frameworks. Angew. Chem. Int. Ed. 2008, 47, 2354-2364.
16. Kleij, A. W. New templating strategies with salen scaffolds (salen = N, N'-Bis (salicylidene) ethylenediamine dianion). Chem. Eur. J. 2008, 14, 10520-10529.
17. Di Mauro, E. F., Kozlowski, M. C. Salen-derived catalysts containing secondary basic groups in the addition of diethylzinc to aldehydes. Org. Lett. 2001, 3, 3053-3056.
18. Jiang, C. J.; Chen, Z. R. Chiral cobalt salen complexes containing Lewis acid: A highly reactive and enantioselective catalyst for the hydrolytic kinetic resolution of terminal epoxides. Kinet. Catal. 2008, 49, 474-478.
19. Hayashi, T., Togni, A., Eds. Ferrocenes; Wiley-VCH Verlag: Weinheim, Germany, 2008.
20. Arrayas, R. G.; Adrio, J.; Carretero, J. C. Recent applications of chiral ferrocene ligands in asymmetric catalysis. Angew. Chem. In. Ed. 2006, 45, 7674-7715.
21. Patti, A.; Pedotti, S. Synthesis of chiral 1-ferrocenylaldols and 1-ferrocenyl-1, 3-diols via asymmetric reduction. Tetrahedron Asymmetry 2006, 17, 1824-1830.
22. Patti, A.; Pedotti, S. Synthesis of chiral alcohols containing the 1, 3-diferrocenylpropane structural motif. Tetrahedron Asymmetry 2008, 19, 1891-1897.
23. Amato, M. E.; Ballistreri, F. P.; Pappalardo, A.; Tomaselli, G. A.; Toscano, R. M.; Williams, D. J. Novel chiral (salen) MnIII complexes containing a calix[4]arene unit as catalysts for enantioselective epoxidation reactions of (Z)-aryl alkenes. Eur. J. Org. Chem. 2005, 3562-3570.
24. Amato, M. E.; Ballistreri, F. P.; Pappalardo, A.; Sciotto, D.; Tomaselli, G. A.; Toscano, R. M. Synthesis and conformational aspects of 20-and 40-membered macrocyclic mono and dinuclear uranyl complexes incorporating salen and (R)-Binol units. Tetrahedron 2007, 63, 9751-9757.
25. Gibson, V. C.; Long, N. J.; Marshall, E. L.; Oxford, P. J.; White, A. J. P.; Williams, D. J. The synthesis and metal coordination chemistry of new 1, 1'-N-substituted ferrocenediyl ligands derived from 1, 1'-diaminoferrocene. J. Chem. Soc. Dalton Trans. 2001, 1162-1164.
26. Shafir, A.; Fiedler, D.; Arnold, J. Formation of 1:1 complexes of ferrocene-containing salen ligands with Mg, Ti and Zr. J. Chem. Soc. Dalton Trans. 2002, 555-560.
27. Gregson, C. K. A.; Gibson, V. C.; Long, N. J.; Marshall, E. L.; Oxford, P. J.; White, A. J. P. Redox control within single-site polymerization catalysts. J. Am. Chem. Soc. 2006, 128, 7410-7411.
28. Wölfle, H.; Kopacka, H.; Wurst, K.; Ongania, K. H.; Görtz, H. H.; Preishuber-Pflügl, P.; Bildstein, B. Planar chiral ferrocene salen-type ligands featuring additional central and axial chirality. J. Organomet. Chem. 2006, 691, 1197-1215.
29. Ballistreri, F. P.; Patti, A.; Pedotti, S.; Tomaselli, G. A.; Toscano, R. M. Synthesis of novel chiral 'salen-type' ferrocenyl ligands. Tetrahedron Asymmetry 2007, 18, 2377-2380.
30. Achard, T.; Belokon, Y. N.; Fuentes, J. A.; North, M.; Parsons, T. Influence of aromatic substituents on metal (II) salen catalysed, asymmetric synthesis of α-methyl α-amino acids. Tetrahedron 2004, 60, 5919-5930.
31. Malinowska, M.; Kwiatkowski, P.; Jurezac, J. The enantioselective high-pressure Diels-Alder reaction of 1-methoxybuta-1, 3-diene with tert-butyldimethylsilyloxy-acetaldehyde catalyzed by (salen) Co (II) and (salen) Cr (III) Cl complexes. Tetrahedron Lett. 2004, 45, 7693-7696.
32. Pedotti, S.; Patti, A. Microwave-assisted synthesis of 1, 5-dioxo-3-substituted [5]ferrocenophanes. J. Organomet. Chem. 2008, 693, 1375-1381.
33. Dalla Cort, A.; Pasquini, C.; Schiaffino, L. Nonsymmetrically substituted uranyl-salophen receptors: New opportunities for molecular recognition and catalysis. Supramol. Chem. 2007, 19, 79-87.
34. Cametti, M.; Dalla Cort, A.; Mandolini, L.; Nissinen, M.; Rissanen, K. Specific recognition of fluoride anion using a metallamacrocycle incorporatine a uranyl-salen unit. New J. Chem. 2008, 32, 1113-1116.
35. Pasini, A.; Gullotti, M.; Cesarotti, E. Schiff base complexes of oxocations-I. Uranyl complexes with tetradentate optically active schiff bases of salicylaldehyde. J. Inorg. Nucl. Chem. 1972, 32, 3821-3833.
36. Kelly, S. M.; Jess, T. J.; Price, N. C. How to study proteins by circular dichroism. BBA-Proteins Proteomics 2005, 1751, 119-139.
37. Berova, N.; Di Bari, L.; Pescitelli, G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem. Soc. Rev. 2007, 36, 914-931.
38. Kypr, J.; Kejnovská, I.; Renčiuk, D.; Vorlíč ková, M. Circular dichroism and conformational polymorphism of DNA. Nucl. Acids Res. 2009, 37, 1713-1725.
39. McCann, D. M.; Stephens, P. J. Determination of absolute configuration using density fuctional theory calculations of optical rotation and electronic circular dichroism: Chiral Alkenes. J. Org. Chem. 2006, 71, 6074-6098.
40. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. The assignment of absolute stereostructures through quantum chemical circular dichroism calculations. Eur. J. Org. Chem. 2009, 2717-2727.
41. Pasini, A.; Gullotti, M.; Ugo, R. Optically active complexes of Schiff bases. Part 4. An analysis of the circular dichroism spectra of some complexes of different coordination numbers with quadridentate Schiff bases of optically active diamines. J. Chem. Soc. Dalton Trans. 1977, 346-356.
42. Hirotsu, M.; Nakajima, K.; Kojima, M.; Yoshikawa, Y. Manganese (III) complexes containing optically active tetradentate Schiff base ligands. Effect of phenyl substituents. Inorg. Chem. 1995, 34, 6173-6178.
43. Szlyk, E.; Surdykowski, A.; Barwiolek, M.; Larsen, E. Spectroscopy and stereochemistry of t6he optically active copper (II), cobalt (II) and nickel (II) complexes with Schiff bases N, N'-(1R, 2R) - (-)-1, 2-cyclohexylenebis (3-methylbenzylideneiminato) and N, N'-(1R, 2R) - (-) 1, 2-cyclohexylenebis-(5- methylbenzylideneiminato). Polyhedron 2002, 21, 2711-2717.
44. Wang, F.; Zhang, H.; Li, L.; Hao, H. Q.; Wang, X. Y.; Chen, J. G. Synthesis and characterization of chiral nickel (II) Schiff base complexes and their CD spectra-absolute configuration correlations. Tetrahedron Asymmetry 2006, 17, 2059-2063.
45. Janowska, I.; Zakrzewski, J. Circular dichroism spectra of planar chiral 2-substituted ferrocenecarboxaldehydes and 2-ferrrocenyl-1, 1-dicyanoethylenes. Tetrahedron Asymmetry 2003, 14, 3271-3273. © 2009