Allylic oxidation catalyzed by chiral dinuclear copper complexes

Tetrahedron

Volumn 54, Issue 21, 1998, Pages 5465-5470

  Fahrni, Christoph J ^a,b  

^a UNIVERSITY OF BASEL   (Switzerland)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; BENZOIC ACID DERIVATIVE; COPPER COMPLEX; CYCLOHEXENE DERIVATIVE; LIGAND;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032554791     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00244-0     Document Type: Article

References (39)

1. 1. a) T. Katsuki, K. B. Sharpless, J. Am. Chem. Soc. 1980, 102, 5974-5976.
2. b) R. A. Johnson, K. B. Sharpless, 'Catalytic Epoxidation of Allylic Alcohols'. In Catalytic Asymmetric Synthesis Ed. I. Ojima, VCH New York, 1993, p. 103-158.
3. 2. a) W. Zhang, J. L. Loebach, S. R. Wilson, E. N. Jacobsen, J. Am. Chem. Soc. 1990, 112, 2801-03.
4. b) For a review, see also: E. N. Jacobsen, 'Asymmetric Epoxidation of Unfunctionalized Olefins'. In In Catalytic Asymmetric Synthesis, Ed. I. Ojima, VCH New York, 1993, p. 159-202.
5. 3. R. A. Johnson, K. B. Sharpless. 'Catalytic Asymmetric Dihydroxylation'. In Catalytic Asymmetric Synthesis, Ed. I. Ojima, VCH New York, 1993, p. 227-272.
6. 4. a) T. Oda, R. Irie, T. Katsuki, H. Okawa, Synlett 1992, 641-642.
7. b) O. J. Gelling, Bimetallic Oxidation Catalysts, University of Groningen 1990.
8. c) M. T. Rispens, C. Zondervan, B. L. Feringa, Tetrahedron: Asymmetry 1995, 6, 661-664.
9. 5. R. Raag, T. L. Poulos, Biochemistry 1989, 28, 917; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537.
10. 5. R. Raag, T. L. Poulos, Biochemistry 1989, 28, 917; A. C. Rosenzweig, C. A. Frederick, S. J. Lippard, P. Nordlund Nature 1993, 366, 537.
11. 6. a) D. H. R. Barton, B. Hu, D. K. Taylor, R. U. Wahl, J. Chem. Soc., Perkin Trans. 2, 1996, 1031; D. H. R. Barton, B. M. Chabot, Tetrahedron 1997, 53, 511.
12. 6. a) D. H. R. Barton, B. Hu, D. K. Taylor, R. U. Wahl, J. Chem. Soc., Perkin Trans. 2, 1996, 1031; D. H. R. Barton, B. M. Chabot, Tetrahedron 1997, 53, 511.
13. 7. a) C. J. Fahrni, A. Pfaltz, Helv. Chim. Acta 1998, 81, 491.
14. b) C. J. Fahrni, M. Neuburger, M. Zehnder, A. Pfaltz, Helv. Chim. Acta 1998, 81, 507.
15. 8. M. S. Kharasch, A. Fono, J. Org. Chem. 1958, 23, 324; M. S. Kharasch, G. Sosnovsky, J. Am. Chem. Soc. 1958, 80, 756.
16. 8. M. S. Kharasch, A. Fono, J. Org. Chem. 1958, 23, 324; M. S. Kharasch, G. Sosnovsky, J. Am. Chem. Soc. 1958, 80, 756.
17. 9. a) J. K. Kochi, J. Am. Chem. Soc. 1961, 83, 3162-63; J. K. Kochi, J. Am. Chem. Soc. 1962, 84, 774-784.
18. 9. a) J. K. Kochi, J. Am. Chem. Soc. 1961, 83, 3162-63; J. K. Kochi, J. Am. Chem. Soc. 1962, 84, 774-784.
19. b) D. Z. Denney, A. Appelbaum, D. B. Denney, J. Am. Chem. Soc. 1962, 84, 4969-4971.
20. c) C. Walling, A. A. Zavitsas, J. Am. Chem. Soc. 1963, 85, 2084-90.
21. 10. A. L. J. Beckwith, A. A. Zavitsas, J. Am. Chem. Soc. 1986, 108, 8230-8234.
22. 11. a) A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831-1834; M. B. Andrus, A. B. Argade, X. Chen, M. G. Pamment, Tetrahedron Lett. 1995, 36, 2945-2948; A. DattaGupta, V. K. Singh, Tetrahedron Lett. 1996, 37, 2633-2636.
23. 11. a) A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831-1834; M. B. Andrus, A. B. Argade, X. Chen, M. G. Pamment, Tetrahedron Lett. 1995, 36, 2945-2948; A. DattaGupta, V. K. Singh, Tetrahedron Lett. 1996, 37, 2633-2636.
24. 11. a) A. S. Gokhale, A. B. E. Minidis, A. Pfaltz, Tetrahedron Lett. 1995, 36, 1831-1834; M. B. Andrus, A. B. Argade, X. Chen, M. G. Pamment, Tetrahedron Lett. 1995, 36, 2945-2948; A. DattaGupta, V. K. Singh, Tetrahedron Lett. 1996, 37, 2633-2636.
25. b) K. Kawasaki, T. Katsuki, Tetrahedron 1997, 53, 6337-6350.
26. c) K. Kawasaki, S. Tsumura, T. Katsuki, Synlett 1995, 1245-1246.
27. 12. a) M. Araki, T. Nagase, Ger. Offen. 26 25030 (1916); Chem. Abstr. 1977, 86, 120886r.
28. 12. a) M. Araki, T. Nagase, Ger. Offen. 26 25030 (1916); Chem. Abstr. 1977, 86, 120886r.
29. b) A. Levina, J. Muzart, Tetrahedron: Asymmetry 1995, 6, 147-156.
30. c) M. J. Södergren, P. G. Andersson, Tetrahedron Lett. 1996, 37, 7577-7580.
31. 13. a) M. Asami, Bull. Chem. Soc. Jpn. 1990, 63, 721-727.
32. b) R. Hayes, T. W. Wallace, Tetrahedron Lett. 1990, 31, 3355.
33. c) A. K. Gupta, R. J. Kazlauskas, Tetrahedron: Asymmetry 1993, 4, 879-888.
34. 14. Z. da Zhang, R. Scheffold, Helv. Chim. Acta 1993, 76, 2602-2615.
35. 15. a) O. Mumm, H. Hesse, H. Volquartz, Chem. Ber. 1915, 48, 379.
36. b) D. Y. Curtin, L. L. Miller, J. Am. Chem. Soc. 1967, 89, 637-645; D. Y. Curtin, L. L. Miller, Tetrahedron Lett. 1965, 7, 1869-1876.
37. b) D. Y. Curtin, L. L. Miller, J. Am. Chem. Soc. 1967, 89, 637-645; D. Y. Curtin, L. L. Miller, Tetrahedron Lett. 1965, 7, 1869-1876.
38. c) J. S. P. Schwarz, J. Org. Chem. 1972, 37, 2906-2908.
39. d) H. Quast, S. Aldenkortt, Chem. Eur. J. 1996, 2, 462.