First TiCl4-mediated diastereoselective reduction of α-nitro ketones to anti-β-nitro alcohols by BH3·SME2

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5854-5857

  Ballini, Roberto ^a   Bosica, Giovanna ^a   Marcantoni, Enrico ^a   Vita, Patrizia ^a   Bartoli, Giuseppe ^b  

^a Via S Agostino 1   (Italy)

^b Dipto Chim Applicata Sci Dei M   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; KETONE DERIVATIVE; TITANIUM DERIVATIVE;

CHELATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; NOTE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0033828564     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000542z     Document Type: Note

References (49)

1. (a) Hakomori, S. In Handbook of Lipid Research Sphingolipid Biochemistry; Kaufer, J. N., Hakomori, S., Eds.; Plenum Pres: New York, 1983; Vol. 1.
2. (b) Williams, T. M.; Crumbie, R.; Mosher, H. S. J. Org. Chem. 1985, 50, 91-97.
3. (c) Rosini, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 321-339.
4. (d) Ballini, R. In Studies in Natural Products Chemistry, Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1997; Vol. 19, pp 117-184.
5. (e) Morgan, B.; Sarikonda, B. R.; Dodds, D. R.; Homan, M. J.; Vail R. Tetrahedron: Asymmetry 1999, 10, 3681-3690.
6. (a) Barrett, A. G. M.; Spilling, C. D. Tetrahedron Lett. 1988, 29, 5733-5734.
7. (b) Bordwell, F. G.; Garbisch, E. W. J. Org. Chem. 1963, 28, 1765-1769.
8. (c) Bordwell, F. G.; Arnold, R. L. J. Org. Chem. 1962, 27, 4426-4428.
9. (d) Nielsen, A. T. J. Org. Chem. 1962, 27, 1998-2001.
10. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
11. (a) Seebach, D.; Colvin, E. W.; Lehr, F.; Weller, T. Chimia 1979, 33, 1-18.
12. (b) Ballini, R.; Bosica, G. J. Org. Chem. 1997, 62, 425-427, and references therein.
13. Bulbule, V. J.; Deshpande, V. H.; Velu, S.; Sudalai, A.; Sivasankar, S.; Sathe, V. T. Tetrahedron 1999, 55, 9325-9332.
14. Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388-7389.
15. (a) Eyer, M.; Seebach, D. J. Am. Chem. Soc. 1985, 107, 3601-3606.
16. (b) Sasai, H.; Suzuki, T.; Arai, S.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1992, 114, 4418-4420.
17. (c) Barrett, A. G. M.; Robyr, C.; Spilling, C. D. J. Org. Chem. 1989, 54, 1233-1234.
18. (d) Kiyooka, S.; Tsutsui, T.; Maeda, H.; Kaneko, Y.; Isobe, K. Tetrahedron Lett. 1995, 36, 6531-6534.
19. (a) Seebach, D.; Leher, F. Angew. Chem., Int. Ed. Engl. 1976, 15, 505-506.
20. (b) Rosini, G.; Ballini, R.; Sorrenti, P.; Petrini, M. Synthesis 1984, 607-608.
21. (c) Rosini, G.; Ballini, R. Synthesis 1988, 833-847.
22. (d) Ono, N.; Fujii, M.; Kaji, A. Synthesis 1987, 532-535.
23. (e) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org. Prep. Proc. Int. 1990, 22, 707-746.
24. (f) Ballini, R.; Bosica, G.; Parrini, M. Tetrahedron Lett. 1998, 39, 7963-7964.
25. (g) Venkat Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149-7152.
26. (h) Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett. 1993, 34, 1859-1862.
27. (i) Cushman, M.; Mathew, J. Synthesis 1982, 397-399.
28. (a) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755.
29. (b) Frye, S. V.; Eliel, E. L.; Cloux, R. J. Am. Chem. Soc. 1987, 109, 1862-1863.
30. (c) Nichols, M. A.; McPhail, A. T.; Arnett, E. M. J. Am. Chem. Soc. 1991, 113, 6222-6233.
31. (d) Still, W. C.; McDonald, J. H. Tetrahedron Lett. 1980, 21, 1031-1034.
32. (e) Keck, G. E.; Abbott, D. E. Tetrahedron Lett. 1984, 25, 1883-1886.
33. (f) Reetz, M. T., Angew. Chem., Int. Ed. Engl. 1984, 23, 556-569.
34. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1994; pp 195-282.
35. Menzel, A.; Ohrlein, R.; Griesser, H.; Wehner, V.; Jäger, V. Synthesis 1999, 1691-1702.
36. (a) Marcantoni, E.; Alessandrini, S.; Malavolta, M.; Bartoli, G.; Bellucci, M. C.; Sambri, L.; Dalpozzo, R. J. Org. Chem. 1999, 64, 1986-1992.
37. (b) Marcantoni, E.; Cingolani, S.; Bartoli, G.; Bosco, M.; Sambri, L. J. Org. Chem. 1998, 63, 3624-3630.
38. (a) Sarko, C. R., Collibee, S. E.; Knorr, A. L.; Di Mare, M. J. Org. Chem. 1996, 61, 868-873.
39. (b) Brown, H. C.; Kanth, J. V. B.; Dalvi, P. V.; Zaidlewicz, H. J. Org. Chem. 1999, 64, 6236-6274, and references therein.
40. Normally, J anti < J syn: Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas, E. Helv. Chim. Acta 1982, 65, 1101-1133.
41. Ballini, R.; Bartoli, G.; Gariboldi, P. V.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1993, 58, 3368-3372.
42. Kingsbury, C. A.; Sopchik, A. E.; Underwood, G.; Rajan, S. J. Chem. Soc., Perkin Trans. 2 1982, 867-874.
43. Kessler, H.; Griesinger, C.; Kerrsenbaum, R.; Wagner, K.; Ernst, R. R. J. Am. Chem. Soc. 1987, 109, 607-609.
44. Dalling, D. K.; Grant, D. M.; Johnson, L. F. J. Am. Chem. Soc. 1971, 93, 3678-3682.
45. Casarini, D.; Lunazzi, L.; Mazzanti, A. J. Org. Chem. 1998, 63, 9125-9127.
46. (a) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
47. (b) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
48. (c) Bernardi, A.; Gennari, C.; Goodman, J. M.; Paterson, I. Tetrahedron: Asymmetry 1995, 6, 2613-2636.
49. (d) Esteve, C.; Ferrero, M.; Romea, P.; Urpì, F.; Vilarrasa, J. Tetrahedron Lett. 1999, 40, 5079-5082.