Synthesis and use of furyl hydroperoxides as reagents in asymmetric oxidations

Current Organic Chemistry

Volumn 8, Issue 7, 2004, Pages 607-621

  Lattanzi, Alessandra ^a   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; CUMENE HYDROPEROXIDE; HYDROPEROXIDE DERIVATIVE; REAGENT; SULFOXIDE; SULFUR DERIVATIVE; TERT BUTYL HYDROPEROXIDE; TITANIUM DERIVATIVE;

ASYMMETRIC CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; ENZYME SYNTHESIS; NONLINEAR SYSTEM; OXIDATION KINETICS; PEROXIDATION; PHOTOOXIDATION; RACEMIC MIXTURE; REVIEW; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; STOICHIOMETRY; STRUCTURE ANALYSIS; SULFOXIDATION; SYNTHESIS;

EID: 1942453238     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272043370799     Document Type: Review

References (57)

1. Hobbs, C. C. Jr.; Houston, B. J. Am. Chem. Soc. 1954, 76, 1254.
2. Schubert, C. C.; Pease, S. J.; Pease, R. N. J. Am. Chem. Soc. 1956, 78 2044.
3. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
4. Kamata, K.; Yonehara, K.; Sumida, Y.; Yamaguchi, K.; Hikichi, S.; Mizuno, N. Science 2003, 300, 964.
5. Ishida, T.; Akiyama, R.; Kobayashi, S. Adv. Synth. Catal., 2003, 345, 576.
6. Shing, T. K. M.; Tai, V. W.-F.; Tam, E. K. W. Angew. Chem., Int. Ed. Engl. 1994, 33, 2312.
7. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
8. Reiser, O. Angew. Chem., Int. Ed. Engl. 1996, 35, 1308.
9. Lempers, H. E. B.; Sheldon, R. A. Applied Catalysis, A: General 1996, 143, 137.
10. Gelalcha, F. G.; Schulze, B. J. Org. Chem. 2002, 67, 8400.
11. Sheldon, R. A. Syntheses and Uses of Alkyl Hydroperoxides and Dialkyl Peroxides, in S. Patai Ed.; The Chemistry of Functional Groups. Peroxides, Wiley: Chichester, 1983.
12. Antonioletti, R.; Bonadies, F.; Scettri, A. Tetrahedron Lett. 1988, 29, 4987.
13. Antonioletti, R.; Bonadies, F.; Floro, C.; Scettri, A. Gazz. Chim. It. 1990, 120, 471.
14. Scettri, A.; Bonadies, F.; Lattanzi, A.; Palombi, L.; Pesci, S. Tetrahedron 1997, 53, 17139.
15. Palombi, L.; Bonadies, F.; Pazienza, A.: Scettri, A. Tetrahedron: Asymmetry 1998, 9, 1817.
16. Lattanzi, A.; Iannece, P.; Scettri, A. Tetrahedron Lett. 1999, 40, 3899.
17. Antonioletti, R.; Bonadies, F.; Principe, T.; Scettri, A. Gazz. Chim. It. 1994, 124, 227.
18. Antonioletti, R.; Bonadies, F.; Monteagudo, E. S.; Rossi, A.; Scettri, A. Tetrahedron Lett. 1992, 33, 1919.
19. Adam, W.; Korb, M. N. Tetrahedron: Asymmetry 1997, 8, 1131.
20. Adam, W.; Humpf, H.; Korb, M. N.; Schreier, P. Tetrahedron: Asymmetry 1997, 8, 3555.
21. Lattanzi, A.; Sagulo, F.; Scettri, A. Tetrahedron: Asymmetry 1999, 10, 2023.
22. Davies, A. G.; Feld, R. J. Chem. Soc. 1956, 665.
23. Kochi, J. K. J. Am. Chem. Soc. 1962, 84, 1193.
24. Massa, A.; Palombi, L.; Scettri, A. Tetrahedron Lett. 2001, 42, 4577.
25. Lattanzi, A.; Iannece, P.; Vicinanza, A.; Scettri, A. Chem. Commun. 2003, 1440.
26. Sharpless, K. B.; Michaelson, R. C. J. Am. Chem. Soc. 1973, 95, 6136.
27. Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 73.
28. Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. Am. Chem. Soc. 1981, 103, 7690.
29. Antonioletti, R.; Bonadies, F.; Lattanzi, A.; Monteagudo, E. S.; Scettri A. Tetrahedron Lett. 1992, 33, 5433.
30. Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1984, 49, 3707.
31. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
32. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
33. Rossiter, B. E. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, pp. 193.
34. Finn, M. G.; Sharpless, K. B. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, pp. 347.
35. Scettri, A.; Bonadies, F.; Lattanzi, A. Tetrahedron: Asymmetry 1996, 7, 629.
36. Lattanzi A.; Bonadies, F.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2141.
37. Pitchen, P.; Duñach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188.
38. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325.
39. Scettri, A.; Bonadies, F.; Lattanzi, A.; Senatore, A.; A. Soriente Tetrahedron: Asymmetry 1996, 7, 657.
40. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
41. Lattanzi, A.; Bonadies, F.; Schiavo, A.; Scettri A. Tetrahedron: Asymmetry 1998, 9, 2619.
42. Lattanzi, A.; Bonadies, F.; Senatore, A.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2473.
43. Höft, E.; Hamann, H.-J.; Kunath, A. J. prakt. Chem. 1994, 336, 534.
44. Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1989, 54, 2085.
45. Kametani, T.; Tsubuki, M.; Honda, T. J. Chem, Soc. Perkin Trans. 1 1990, 639.
46. Massa, A.; Lattanzi, A.; Siniscalchi, F.; Scettri A. Tetrahedron: Asymmetry 2001, 12, 2775.
47. Massa, A.; Siniscalchi, F. R.; Bugatti, V.; Lattanzi, A.; Scettri A. Tetrahedron: Asymmetry 2002, 13, 1277.
48. Komatsu, N.; Hashizume, M.; Sugita, T. Uemura, S. J. Org. Chem. 1993, 58, 4529.
49. Lattanzi, A.; Iannece, P.; Scettri, A. Tetrahedron Lett. 2002, 43, 5629.
50. Adam, W.; Korb, M. N.; Roschmann, K. J.; Saha-Möller, C. R. J. Org. Chem. 1998, 63, 3423.
51. Martin, V. C.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237.
52. Aoki, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 187.
53. Adam, W.; Alsters, P. L.; Neumann, R.; Saha-Möller, C. R.; Seebach, D.; Zhang, R. Org. Lett. 2003, 5, 725.
54. Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922.
55. Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. Engl. 2000, 112, 3532.
56. Kagan, H. B. Synlett 2001, 888.
57. Puchot, C.; Samuel, O.; Dunach, E.; Zhao, S.; Agami, C.; Kagan, H. B. J. Am. Chem. Soc. 1986, 108, 2353.