Enantioselective oxidation of secondary alcohols using a chiral nitroxyl (N-oxoammonium salt) catalyst

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1194-1195

  Rychnovsky, Scott D ^a   McLernon, Terri L ^a   Rajapakse, Hemaka ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000769191     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9522320     Document Type: Article

References (30)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons, Inc.: New York, 1994.
2. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, U.K., 1994.
3. Far a discussion of resolutions using HLADH, see: Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. In Advances in the Use of Synthons in Organic Chemistry; Donodoni, S., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 1, pp 143-219.
4. For example, see: (a) Ohkubo, K.; Hirata, K.; Yoshinaga, K. Chem. Lett. 1976, 577-578. (b) Beckett, M. A.; Homer, R. B. Inorg. Chim. Acta 1986, 122, L5-L7. (c) Ishii, Y.; Suzuki, K.; Ikariya, T.; Saburi, M.; Yoshikawa, S. J. Org. Chem. 1986, 51, 2822-2824. (d) Perkins, M. J.; Berti, C.; Brooks, P. J.; Grierson, L.; Grimes, J. A.-M.; Jenkins, T. C., Smith, S. L. Pure Appl. Chem. 1990, 62, 195-200.
5. For example, see: (a) Ohkubo, K.; Hirata, K.; Yoshinaga, K. Chem. Lett. 1976, 577-578. (b) Beckett, M. A.; Homer, R. B. Inorg. Chim. Acta 1986, 122, L5-L7. (c) Ishii, Y.; Suzuki, K.; Ikariya, T.; Saburi, M.; Yoshikawa, S. J. Org. Chem. 1986, 51, 2822-2824. (d) Perkins, M. J.; Berti, C.; Brooks, P. J.; Grierson, L.; Grimes, J. A.-M.; Jenkins, T. C., Smith, S. L. Pure Appl. Chem. 1990, 62, 195-200.
6. For example, see: (a) Ohkubo, K.; Hirata, K.; Yoshinaga, K. Chem. Lett. 1976, 577-578. (b) Beckett, M. A.; Homer, R. B. Inorg. Chim. Acta 1986, 122, L5-L7. (c) Ishii, Y.; Suzuki, K.; Ikariya, T.; Saburi, M.; Yoshikawa, S. J. Org. Chem. 1986, 51, 2822-2824. (d) Perkins, M. J.; Berti, C.; Brooks, P. J.; Grierson, L.; Grimes, J. A.-M.; Jenkins, T. C., Smith, S. L. Pure Appl. Chem. 1990, 62, 195-200.
7. For example, see: (a) Ohkubo, K.; Hirata, K.; Yoshinaga, K. Chem. Lett. 1976, 577-578. (b) Beckett, M. A.; Homer, R. B. Inorg. Chim. Acta 1986, 122, L5-L7. (c) Ishii, Y.; Suzuki, K.; Ikariya, T.; Saburi, M.; Yoshikawa, S. J. Org. Chem. 1986, 51, 2822-2824. (d) Perkins, M. J.; Berti, C.; Brooks, P. J.; Grierson, L.; Grimes, J. A.-M.; Jenkins, T. C., Smith, S. L. Pure Appl. Chem. 1990, 62, 195-200.
8. Bobbitt reported enantioselective oxidations of 1-phenylethanol (turnover = 0.3, S = 3.3) and cis-1,2-cyclohexanedimethanol (turnover = 3.6, S = 2.2). Ma, Z.; Huang, Q.; Bobbitt, J. M. J. Org. Chem. 1993, 58, 4837-4843.
9. Semmelhack, M. F.; Schmid, C. R.; Cortes, D. S. Tetrahedron Lett. 1986, 27, 1119-1122.
10. (a) Cella, J. A.; Kelley, J. A.; Kenehan, E. F. J. Org. Chem. 1975, 40, 1860-1862.
11. (b) Ganem, B. J. Org. Chem. 1975, 40, 1998-2000.
12. (a) Semmelhack, M. F.; Chou, C. S.; Cortes, D. S. J. Am. Chem. Soc. 1983, 105, 4492-4494.
13. (b) Inokuchi, T.; Matsumoto, S.; Torii, S. J. Org. Chem. 1991, 56, 2416-2421.
14. (a) Anelli, P. L.; Biffi, C.; Montanari, F.; Quici, S. J. Org. Chem. 1987, 52, 2559-2562.
15. (b) Anelli, P. L.; Montanari, F.; Quici, S. Org. React. 1990, 69, 212-219.
16. For an alternate mechanistic proposal see: Ma, Z; Bobbitt, J. M. J. Org. Chem. 1991, 56, 6110-6114.
17. 3)]. Maigrot, N.; Mazaleyrat, J. P.; Welvart, Z. J. Org. Chem. 1985, 50, 3916-3918.
18. (a) Hawkins, J. M.; Fu, G. C. J. Org. Chem. 1986, 51, 2820-2822.
19. (b) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1992, 57, 2114-2121.
20. (c) Hawkins, J. M.; Lewis, T. A. J. Org. Chem. 1994, 59, 649-652.
21. Meyers reported an independent synthesis of 3 using his enantioselective aryl coupling and alkylation: Meyers, A. I.; Nguyen, T. H. Tetrahedron Lett. 1995, 36, 5873-5876.
22. Fraser, R. R.; Boussard, G.; Postescu, I. D.; Whiting, J. J.; Wigfield, Y. Y. Can. J. Chem. 1973, 51, 1109-1115.
23. 2)]. Mosher's analysis showed none of the minor enantiomer.
24. 3).
25. Anelli, P. L.; Banfi, S.; Montanari, F.; Quici, S. J. Org. Chem. 1989, 54, 2970-2972
26. S = In[(1 - C)(1 - ee)]/In[(1 - C)(1 + ee)] where ee is the fractional enantiomeric excess and C is the conversion. For an excellent discussion of kinetic resolutions, see: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
27. Lee, G. A.; Freedman, H. H. Tetrahedron Lett. 1976, 1641.
28. We thank Mr. Timothy Richardson for performing this experiment.
29. x. The transition state atoms were frozen, and the complete transition state for the reaction of (R)- and (S)-1-phenylethanol with the W-oxoammonium salt of 1 was assembled around this frozen core and minimized at the AM1 level. The calculated TS energy for (S)-1-phenylethanol was 161.70 kcal/mol, while the TS energy for (R)-1-phenylethanol was 162.27 kcal/mol. Details of these calculations will be presented elsewhere.
30. Balfe, M. P.; Downer, E. A. W.; Evans, A. A.; Kenyon, J.; Poplett, R.; Searle, C. E.; Tarnoky, A. L. J. Chem. Soc. 1946, 787-803.