Novel unsymmetric chiral Schiff bases possessing two different donor moieties: Unique tetradentate ligands from combination of salicylaldehyde and acetylacetone units

Tetrahedron Asymmetry

Volumn 9, Issue 21, 1998, Pages 3741-3744

  Lopez, Jose ^a   Mintz, Eric A ^a   Hsu, Fu Liang ^b   Bu, Xiu R ^a  

^a CLARK ATLANTA UNIVERSITY   (United States)

^b U S ARMY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLACETONE; LIGAND; SALICYLALDEHYDE;

ARTICLE; CATALYST; CHIRALITY; CONJUGATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0032491548     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00401-7     Document Type: Article

References (11)

1. Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
2. Also see: Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345; Tokunage, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
3. Also see: Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345; Tokunage, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
4. Lopez, J.; Liang, S.; Bu, X. R. Tetrahedron Lett. 1998, 39, 4199.
5. 2: C: 72.04, H: 7.81. Calcd C: 72.00, H: 8.00.
6. Rogers, M. T.; Burdett, J. L. Can. J. Chem. 1965, 43, 1516. Also see: Gero, A. J. Org. Chem. 1954, 19, 469.
7. Rogers, M. T.; Burdett, J. L. Can. J. Chem. 1965, 43, 1516. Also see: Gero, A. J. Org. Chem. 1954, 19, 469.
8. Sardella, D. J.; Heinert, D. H.; Shapiro, B. L. J. Org. Chem. 1969, 34, 2817.
9. The chiral half unit 5: 3,5-di-t-butylsalicylaldehyde (6.38 mmol) in chloroform (50 mL) was added dropwise over 5 hours to a vigorously stirred solution of (1R,2R)-(-)-diaminocyclohexane (6.38 mmol) in chloroform (150 mL) containing 4 Å molecular sieves at 0°C to give a yellow solid, yield 1.94 g, 93%. For the detailed work-up, see Ref. 3.
10. Normal rate: addition completed within 5-10 minutes; slow rate: addition completed over 1 hour. All the reactions for trifluoromethyl-containing 1,3-diketones are run in anhydrous solvents.
11. For recent leading references for interaction of Schiff base complexes with DNA: Gravert, D. L.; Griffin, J. H. Inorg. Chem. 1996, 35, 4837.