Catalytic reactions of titanium alkoxides with Grignard reagents and imines: A mechanistic study

Chemistry - An Asian Journal

Volumn 5, Issue 8, 2010, Pages 1830-1837

  Kumar, Akshai ^a   Samuelson, Ashoka G ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Alkylation; Catalysis; Grignard reagents; Isotopic labeling; Titanium isopropoxide

Indexed keywords

ALKYL COMPLEXES; ALKYLATING AGENTS; CATALYTIC REACTIONS; GRIGNARD REAGENT; ISOTOPIC LABELING; LABELED SUBSTRATES; MECHANISTIC STUDIES; OLEFIN COMPLEXES; REDUCTIVE COUPLINGS; REDUCTIVE ELIMINATION; STOICHIOMETRIC REACTION; TITANIUM ALKOXIDES; TITANIUM ISOPROPOXIDE;

ALKYLATION; CATALYSIS; DEUTERIUM; MECHANICS; NITROGEN COMPOUNDS; OLEFINS; REACTION INTERMEDIATES; TITANIUM;

TITANIUM COMPOUNDS;

IMINE; ORGANOMETALLIC COMPOUND; TITANIUM ISOPROPOXIDE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKYLATION; CATALYSIS; IMINES; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS;

EID: 77955206075     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900711     Document Type: Article

References (51)

1. a) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069-1094;
2. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293.
3. H. Deng, J.-K. Jung, T. Liu, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 9032-9034.
4. K. Tomioka, I. Inoue, M. Shindo, K. Koga, Tetrahedron Lett. 1990, 31, 6681-6684.
5. a) Z.-L. Shen, H.-L. Cheong, T.-P. Loh, Chem. Eur. J. 2008, 14, 1875-1880;
6. Z.-L. Shen, T.-P. Loh, Org. Lett. 2007, 9, 5413-5416.
7. a) X. L. Hou, X. L. Zheng, L. X. Dai, Tetrahedron Lett. 1998, 39, 6949-6952;
8. R. Almansa, D. Guijaro, M. Yus, Tetrahedron: Asymmetry 2007, 18, 2828-2840;
9. R. Almansa, D. Guijaro, M. Yus, Tetrahedron 2007, 63, 1167-1174.
10. a) M. Hatano, S. Suzuki, K. Ishihara, J. Am. Chem. Soc. 2006, 128, 9998-9999;
11. G. K. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541-2569.
12. a) M. Shi, C.-J. Wang, Adv. Synth. Catal. 2003, 345, 971-973;
13. C.-J. Wang, M. Shi, J. Org. Chem. 2003, 68, 6229-6237;
14. X. Li, L. F. Cun, L. Z. Gong, A. Q. Mi, Y. Z. Jiang, Tetrahedron: Asymmetry 2003, 14, 3819-3821;
15. T. Soeta, K. Nagai, H. Fijihara, M. Kuriyama, K. Tomioka, J. Org. Chem. 2003, 68, 9723-9727;
16. B. C. Andre, A. B. Alessandro, C. Alexandre, M. Elaine, P. Julien, D. Jean-Nicolas, L. Claude, Pure Appl. Chem. 2005, 77, 1259-1267;
17. D. Ferraris, Tetrahedron 2007, 63, 9581-9597;
18. J. Esquivias, R. G. Arrayas, J. C. Carretero, J. C. Carlos, Angew. Chem. 2007, 119, 9417-9420;
19. Angew. Chem. Int. Ed. 2007, 46, 9257-9260;
20. M. G. Pizzuti, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2008, 73, 940-947;
21. Q. Perron, A. Alexakis, Tetrahedron: Asymmetry 2008, 19, 1871-1874;
22. K. Yamada, K. Tomioka, Chem. Rev. 2008, 108, 2874-2886.
23. Y. N. Belokon, R. G. Davies, J. A. Fuentes, M. North, T. Parsons, Tetrahedron Lett. 2001, 42, 8093-8096.
24. a) H. Nakamura, K. Nakamura, Y. Yamamoto, J. Am. Chem. Soc. 1998, 120, 4242-4243;
25. H. Nakamura, K. Nakamura, Y. Yamamoto, J. Org. Chem. 1999, 64, 2614-2615;
26. H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641-6647;
27. R. K. Sharma, A. G. Samuelson, J. Chem. Sci. 2006, 118, 569-573.
28. a) G. R. Cook, R. Kargbo, B. Maity, Org. lett. 2005, 7, 2767-2770;
29. R. Kargbo, Y. Takahashi, S. Bhor, G. R. Cook, G. C. Lloyd-Jones, I. R. Shepperson, J. Am. Chem. Soc. 2007, 129, 3846-3847;
30. R. B. Kargbo, G. R. Cook, Curr. Org. Chem. 2007, 11, 1287-1309;
31. D. Samanta, R. B. Kargbo, G. R. Cook, J. Org. Chem. 2009, 74, 7183-7186.
32. B. C. Andre, G. Alexandre, Tetrahedron: Asymmetry 1999, 10, 1961-1968.
33. E. Dieters, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946.
34. a) T. Tamotsu, L. Yuanhong, X. Chanjuan, H. Shouquan, Chem. Commun. 2001, 31-32;
35. V. Gandon, P. Bertus, J. Szymoniak, Eur. J. Org. Chem. 2001, 3677-3681.
36. a) C. A. Laura, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 2003, 115, 4376-4379;
37. Angew. Chem. Int. Ed. 2003, 42, 4244-4247;
38. R. P. James, F. T. John, A. H. Hoveyda, M. L. Snapper, J. Am. Chem. Soc. 2001, 123, 984-985;
39. F. T. John, A. H. Hoveyda, M. L. Snapper, Org. Lett. 2003, 5, 3273-3275;
40. C. A. Laura, R. P. James, F. T. John, M. L. Snapper, A. H. Hoveyda, Adv. Synth. Catal. 2005, 347, 417-425;
41. P. Fu, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2008, 130, 5530-5541.
42. G. Thomas, I. Haruro, A. Ryo, S. Kobayashi, Angew. Chem. 2001, 113, 1949-1951;
43. Angew. Chem. Int. Ed. 2001, 40, 1896-1898.
44. J. J. Eisch, J. N. Gitua, Organometallics 2003, 22, 24-26.
45. J. J. Eisch, S. Dutta, Organometallics 2005, 24, 3355-3358.
46. a) C. Laroche, P.-R. Richard, S. Jan, P. Bertus, J.-B. Behr, Synlett 2006, 2, 223-226;
47. C. Laroche, J.-B. Behr, S. Jan, P. Bertus, P.-R. Richard, Eur. J. Org. Chem. 2005, 5084-5088;
48. F. Sato, H. Urabe, Titanium and Zirconium in Organic Synthesis, Wiley-VCH, Weinheim, 2002, pp. 319-354.
49. K. Neuvonen, F. Flp, H. Neuvonen, A. Koch, E. Kleinpeter, K. Pihlaja, J. Org. Chem. 2003, 68, 2151-2160.
50. B. Schimidt, D. Seebach, Angew. Chem. 1991, 103, 1383-1385;
51. Angew. Chem. Int. Ed. Engl. 1991, 30, 1321-1323.