Ligand-Assisted Rate Acceleration in Transacylation by a Yttrium - Salen Complex. Demonstration of a Conceptually New Strategy for Metal-Catalyzed Kinetic Resolution of Alcohols

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1607-1610

  Lin, Mei Huey ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

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EID: 0000469464     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025809q     Document Type: Article

References (28)

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7. (g) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Kinetic resolution of a diol: Iwasaki, F.; Maki, T.; Nakashima, W.; Onomura, O.; Matsumura, Y. Org. Lett. 1999, 1, 969. For a novel oxidative kinetic resolution, see: Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
8. (g) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Kinetic resolution of a diol: Iwasaki, F.; Maki, T.; Nakashima, W.; Onomura, O.; Matsumura, Y. Org. Lett. 1999, 1, 969. For a novel oxidative kinetic resolution, see: Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
9. (g) Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169. Kinetic resolution of a diol: Iwasaki, F.; Maki, T.; Nakashima, W.; Onomura, O.; Matsumura, Y. Org. Lett. 1999, 1, 969. For a novel oxidative kinetic resolution, see: Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
10. Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2000, 2, 997. For an example of a lanthanide-catalyzed transesterification, see: Okano, T.; Miyamoto, K.; Kiji, J. Chem. Lett. 1995, 246.
11. Lin, M.-H.; RajanBabu, T. V. Org. Lett. 2000, 2, 997. For an example of a lanthanide-catalyzed transesterification, see: Okano, T.; Miyamoto, K.; Kiji, J. Chem. Lett. 1995, 246.
12. See Supporting Information for a more complete list of ligands, their preparation and characterization, and experimental details ot their utility in various acyl transfer reactions.
13. 1): (a) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; p 649. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
14. 1): (a) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; p 649. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
15. 1): (a) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; p 649. Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
16. 3):
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20. (a) Herrmann, W. A.; Anwander, R.; Munck, F. C.; Scherer, W.; Dufaud, V.; Huber, N. W.; Artus, G. R. J. Z. Naturforsch., B: Chem. Sci. 1994, 49, 1789.
21. (b) Runte, O.; Priermeier, T.; Anwander, R. J. Chem. Soc., Chem. Commun. 1996, 1385.
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23. Typical Experimental Procedure for Transacylation. A mixture of alcohol (1 mmol) and the Y-catalyst in toluene (1.5 mL) was cooled to the indicated temperature under nitrogen, and the enol acetate (1.27 mmol) was added. At the end of the prescribed time, the cold solution was poured into water, and the products were extracted with ether. The ether solution was washed with saturated NaCl and dried, and the products were isolated by column chromatography. The ee's of unreacted alcohols were determined by chiral HPLC. See Supporting Information for details.
24. Crystallographic data (excluding structure factors) for the structure of 1 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-181773. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB12EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ ccdc.cam.ac.uk. See Supporting Information for details.
25. For a related complex, see ref 5c.
26. For a leading reference, see: Evans, D. A.; Johnson, J. S. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; p 1177.
27. Kasan, H. B.; Fiaud, J. C. Topics Stereochem. 1988, 18, 249.
28. The following ketones (with their s values shown in the bracket) were tested the for acylation of 1-indanol: tert-butyl methyl ketone (1.33, 22°C), 4-methylacetophenone (1.30, 22°C), isobutyraladehyde (2.60, -3 °C), cyclohexanone (1.67. -15°C), (-)-menthone (1.5. -15°C), and camphor (1.00, -15°C). Most remarkably, the enolacetate derived from (+)-menthone showed no reactivity at -15°C (0% conversion!) under conditions where the corresponding (-)-menthone enolacetate gave 59% conversion. We saw the same behavior in the acylation of α-tetralol but not in the acyclic alcohols. See Supporting Information for details.