Unsymmetric chiral Salen Schiff bases: A new chiral ligand pool from Bis-Schiff bases containing two different salicylaldehyde units

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4199-4202

  Lopez, Jose ^a   Liang, Sidney ^a   Bu, Xiu R ^a  

^a CLARK ATLANTA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SALICYLALDEHYDE; SCHIFF BASE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS;

EID: 0032508084     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00784-9     Document Type: Article

References (18)

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5. (b) Li, Z.; Conster, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326. 7. Nagajima, K.; Kojima, M.; Fujita, J. Chem. Lett. 1986, 1483.
6. (c) Yamashita, Y.; Katsuki, T. Synlett 1995, 829.
7. (d) Martinez, Leighton, J. L.; Carsten, D. H.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5898.
8. (e). Also see: kinetic resolution of terminal epoxides with Salen-Co(III) catalyst by Tokunage, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936.
9. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
10. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
11. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
12. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
13. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
14. 4. Jacobsen, E. N.; Zhang, W.; Güler, M. J. Am. Chem. Soc. 1991, 113, 6703. Also see: Jacobsen, E. N. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L. S., Eds.; Pregamon: New York, 1995, vol. 12. and Katsuki, T. Coord. Chem. Rev. 1995, 140, 189. Also see: Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 42, 7739. Zhao, S.-H.; Ortiz, P. R.; Keys, B. A.; Davenprot, K. G. Tetrahedron Lett. 1996, 37, 2725.
15. 5. A racemic compound with similar structure was proposed from a reaction which took a week, see: Matsumoto, N.; Nozaki, T.; Ushio, H.; Motoda, K.-i.; Ohba, M.; Mago, G.; Okawa, H. J. Chem. Soc. Dalton Trans. 1993, 2157.
16. 3/TMS): 165.1, 164.9, 161.5, 161.3, 132.6, 132.5, 131.8, 131.7, 119.0, 118.9, 117.4, 117.3, 117.1, 73.2, 55.0, 34.0, 33.8, 33.5, 25.2, 25.0, 24.5 ppm.
17. 2: C: 78.89, H: 8.33, Calc. C: 78.92, H: 7.94.
18. 8. Liang, S.; Santos, J.; Bu, X. R. Mintz, E., manuscript in preparation.