Efficient diastereoselective titanium(IV) reductive amination of ketones

Letters in Organic Chemistry

Volumn 3, Issue 5, 2006, Pages 384-389

  Salmi, Chanaz ^a   Letourneux, Yves ^a   Brunel, Jean Michel ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Diastereoselectivity; Imines; Ketones; Reductive amination; Secondary amines; Titanium

Indexed keywords

EID: 33746116854     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806776611971     Document Type: Article

References (52)

1. Brunel, J. M. Recent Res. Devel. Organic Chem. 2003, 7, 155.
2. Emerson, W. S. Org. React. 1948, 4, 174.
3. Lane, C. F. Synthesis 1975, 135.
4. Hutchins, R. O.; Hutcgins, M. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 8, pp. 25.
5. Whitesell, J. K. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 6, pp. 724.
6. Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
7. Johansson, A. Contemp. Org. Synth. 1995, 393.
8. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
9. Spindler, F.; Blaser, H. U. In Transition Metals in Organic Synthesis; Beller, M.; Bolm, C. Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2, pp. 69.
10. Bringmann, G. The Alkaloids, Brossi, A. Ed., Academic Press: New-York, 1986; Vol. 29.
11. Blaser, H. U.; Spindler, F. Chimia 1997, 51, 297.
12. Danishefsky, S. J.; Harrisson, P. J.; Webb, R. R.; O'Neill, B. T. J. Am. Chem. Soc. 1985, 107, 1421.
13. Lu, S. T.; Su, T. L.; Kametani, T.; Ujie, A.; Ihara, M.; Fukumoto, K. Heterocycles 1975, 3, 459.
14. Lu, S. T.; Wang, E. C. Phytochemistry 1982, 21, 809.
15. Menachery, M. P.; Lavanier, G. L.; Wetherly, M. L.; Guinaudeau, H.; Shamma, M. J. Nat. Prod. 1986, 49, 745.
16. Moser, H.; Rihs, G.; Sauter, H. Naturfosch 1982, 376, 451.
17. Vagt, U. Chimica Oggi 1998, 16, 38.
18. Yurovskaya, M. A.; Karchava, A. V. Tetrahedron: Asymmetry 1998, 9, 3331.
19. Borg, G.; Cogan, D. A.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709.
20. Moss, N.; Gauthier, J.; Ferland, J. M. Synlett 1995, 142.
21. Bhattacharyya, S. Tetrahedron Lett. 1994, 35, 2401.
22. Bhattacharyya, S. J. Chem. Soc., Perkin Trans I 1995, 1845.
23. Bhattacharyya, S. Synth. Commun. 1995, 25, 9.
24. Bhattacharyya, S. Synth. Commun. 2000, 30, 2001.
25. Bhattacharyya, S.; Chatterjee, A.; Williamson, J. S. Synlett 1995, 1079.
26. Kumpaty, H. J.; Williamson, J. S.; Bhattaharyya, S. Synth. Commun. 2003, 33, 1411.
27. Miriyala, B.; Bhattacharyya, S.; Williamson, J. S. Tetrahedron 2004, 60, 1463.
28. Neidigh, K. A.; Avery, M. A.; Williamson, J. S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans I 1998, 2527.
29. Alexakis, A.; Gille, S.; Prian, F.; Rosset, S.; Ditrich, K. Tetrahedron Lett. 2004, 45, 1449.
30. 4 [19,20] or the titanium asymmetric reductive amination reaction using chiral ketones [31-36].
31. Bisel, P.; Breitling, E.; Frahm, W. Eur. J. Org, Chem. 1998, 729.
32. Cimarelli, C.; Palmieri, G. Tetrahedron Asymmetry 2000, 11, 2555.
33. Bringmann, G.; Geisler, J. P.; Geuder, T.; Kunkel, G.; Kinzinger, L. Liebigs Ann. Chem. 1990, 795.
34. Marx, E.; EL Bouz, M.; Celerier, J. P.; Lhommet, G. Tetrahedron Lett. 1992, 33, 4307
35. Nugent, T. C., Seemayer, R. Org. Process Res. Dev. 2006, 10, 142.
36. Dhainaut, J.; Leon, P.; Lher-Mitte, F.; Oddon, G. Merial SAS, France, Patent Number WO0192281, 2001.
37. During the submission of our article, significant complementary results appeared on the evolution of Titanium(IV) alkoxides and Raney nickel for asymmetric reductive amination of prochiral aliphatic ketones with good to excellent diastereoselectivities. Nugent, T. C.; Wakchaure, V. N.; Ghosh, A. K.; Mohanty, R. R. Org. Lett. 2005, 7, 4967.
38. It is noteworthy that such solvents have been recently successfully used in the Titanium reductive amination reaction applied to solid phase synthesis. DiCesare, J. C.; White, C. E.; Rasmussen, W. E.; White, B. M.; McComas, C. B.; Craft, L. E. Synth. Commun. 2005, 35, 663.
39. 13C NMR spectroscopy by analogy with methods previously reported by Snyder [40], Winberg [41,42] and Alexakis [43,44] allowing an accurate measure of the diastereoselectivity.
40. Toldes, M.; Snyder, J. Y, Tetrahedron Lett. 1988, 29, 6063.
41. Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 18, 2183.
42. Lemiere, G. L.; Dommisse, R. A.; Lepoivre, J. A.; Alderweireldt, F. C.; Hiemstra, H.; Wynberg, H.; Jones, J. B.; Toone, E. J. J. Am. Chem. Soc. 1987, 109, 1363.
43. Alexakis, A.; Frutos, J. C.; Mangeney, P. Tetrahedon: Asymmetry 1993, 4, 2431.
44. Alexakis, A.; Frutos, J. C.; Mutti, S.; Mangeney, P. J. Org. Chem. 1994, 59, 3326.
45. Cimarelli, C.; Palmieri, G.; Volpini, E. J. Org. Chem. 2003, 68, 1200.
46. Edwards, A. J.; Hockey, S.; Mair, F. S.; Raithby, P. R.; Snaith, R.; Simpkins, N. S. J. Org. Chem. 1993, 58, 6942.
47. Chang, Z. Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3464.
48. Marshall, J. A.; Lebreton, J. J. Am. Chem. Soc. 1988, 110, 2925.
49. Eleveld, M. B.; Hogeveen, H.; Schudle, E. P. J. Org. Chem. 1986, 51, 3635.
50. Alvaro, G.; Savoia, D.; Valentinetti, M. R. Tetrahedron 1996, 52, 12571.
51. Mattson, R. J.; Pham, K. M.; Leuck, D. J.; Cowen, K. A. J. Org. Chem. 1990, 55, 2552.
52. A detailed mechanistic study will appear in due course. Salmi, C.; Letourneux, Y.; Brunei, J. M. Leff. Org. Chem. in press