Direct titanium-mediated conversion of ketones into enamides with ammonia and acetic anhydride

Angewandte Chemie - International Edition

Volumn 51, Issue 6, 2012, Pages 1400-1404

  Reeves, Jonathan T ^a   Tan, Zhulin ^a   Han, Zhengxu S ^a   Li, Guisheng ^a   Zhang, Yongda ^a   Xu, Yibo ^a   Reeves, Diana C ^a   Gonnella, Nina C ^a   Ma, Shengli ^a   Lee, Heewon ^a   Lu, Bruce Z ^a   Senanayake, Chris H ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

ammonia; enamides; synthetic methods; titanium

Indexed keywords

ACETIC ANHYDRIDES; ALKOXIDES; ENAMIDES; ETHYLENE DIAMINE; SYNTHETIC METHODS; TETRAKIS; WATER SOLUBILIZATION;

AMMONIA; FUNCTIONAL GROUPS; KETONES;

TITANIUM;

ACETIC ANHYDRIDE; AMIDE; AMMONIA; KETONE; TITANIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETIC ANHYDRIDES; AMIDES; AMMONIA; COMBINATORIAL CHEMISTRY TECHNIQUES; KETONES; MOLECULAR STRUCTURE; STEREOISOMERISM; TITANIUM;

EID: 84863011655     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107601     Document Type: Article

References (78)

1. J.-H. Xie, S.-F. Zhu, Q.-L. Zhou, Chem. Rev. 2011, 111, 1713-1760
2. T. C. Nugent, M. El-Shazly, Adv. Synth. Catal. 2010, 352, 753-819
3. S. Enthaler, G. Erre, K. Junge, D. Addis, R. Kadyrov, M. Beller, Chem. Asian J. 2008, 3, 1104-1110
4. H. U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103-151
5. W. Tang, X. Zhang, Chem. Rev. 2003, 103, 3029-3069
6. M. vandenBerg, R. M. Haak, A. J. Minnaard, A. H. M. deVries, J. G. deVries, B. L. Feringa, Adv. Synth. Catal. 2002, 344, 1003-1007.
7. K. Zheng, X. Liu, J. Zhao, Y. Yang, L. Lin, X. Feng, Chem. Commun. 2010, 46, 3771-3773
8. M. Terada, K. Machioka, K. Sorimachi, Angew. Chem. 2006, 118, 2312-2315
9. Angew. Chem. Int. Ed. 2006, 45, 2254-2257
10. R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem. 2004, 116, 1711-1713
11. Angew. Chem. Int. Ed. 2004, 43, 1679-1681.
12. L. Zu, H. Xie, H. Li, J. Wang, X. Yu, W. Wang, Chem. Eur. J. 2008, 14, 6333-6335
13. F. Berthiol, R. Matsubara, N. Kawai, S. Kobayashi, Angew. Chem. 2007, 119, 7949-7951
14. Angew. Chem. Int. Ed. 2007, 46, 7803-7805.
15. Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, L.-Z. Gong, Org. Lett. 2009, 11, 4620-4623
16. C. Baudequin, A. Zamfir, S. B. Tsogoeva, Chem. Commun. 2008, 4637-4639
17. Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem. 2007, 119, 5661-5663
18. Angew. Chem. Int. Ed. 2007, 46, 5565-5567.
19. R. A. Hughes, S. P. Thompson, L. Alcaraz, C. J. Moody, J. Am. Chem. Soc. 2005, 127, 15644-15651
20. Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076-4079
21. Angew. Chem. Int. Ed. 2008, 47, 4012-4015.
22. H. Zhou, Y.-H. Xu, W.-J. Chung, T.-P. Loh, Angew. Chem. 2009, 121, 5459-5461
23. Angew. Chem. Int. Ed. 2009, 48, 5355-5357.
24. J. Chen, W. Zhang, H. Geng, W. Li, G. Hou, A. Lei, X. Zhang, Angew. Chem. 2009, 121, 814-816
25. Angew. Chem. Int. Ed. 2009, 48, 800-802
26. P. Dupau, P. LeGendre, C. Bruneau, P. H. Dixneuf, Synlett 1999, 1832-1834
27. D. M. Tschaen, L. Abramson, D. Cai, R. Desmond, U.-H. Dolling, L. Frey, S. Karady, Y.-J. Shi, T. R. Verhoeven, J. Org. Chem. 1995, 60, 4324-4330; from ketals
28. M. Sugawara, K. Inoue, M. Yasutake, I. D. Gridnev, N. Azuma, T. Imamoto, (Kanegafuchi Chemical Industry Co., Ltd., Japan), Jpn. Kokai Tokkyo Koho, 2002308842, 2002.
29. D. J. Wallace, K. R. Campos, C. S. Shultz, A. Klapars, D. Zewge, B. R. Crump, B. D. Phenix, J. C. McWilliams, S. Krska, Y. Sun, C.-y. Chen, F. Spindler, Org. Process Res. Dev. 2009, 13, 84-90
30. M. C. Willis, G. N. Brace, I. P. Holmes, Synthesis 2005, 3229-3234
31. A. Klapars, K. R. Campos, C. Chen, R. P. Volante, Org. Lett. 2005, 7, 1185-1188
32. R. S. Coleman, P.-H. Liu, Org. Lett. 2004, 6, 577-580
33. L. Jiang, G. E. Job, A. Klapars, S. L. Buchwald, Org. Lett. 2003, 5, 3667-3669
34. D. J. Wallace, D. J. Klauber, C. Chen, R. P. Volante, Org. Lett. 2003, 5, 4749-4752.
35. Z. Liu, D. Xu, W. Tang, L. Xu, J. Mo, J. Xiao, Tetrahedron Lett. 2008, 49, 2756-2760
36. A. L. Hansen, T. Skrydstrup, J. Org. Chem. 2005, 70, 5997-6003
37. P. Harrison, G. Meek, Tetrahedron Lett. 2004, 45, 9277-9280.
38. Y. Bolshan, R. A. Batey, Tetrahedron 2010, 66, 5283-5294
39. R. R. Cesati III, G. Dwyer, R. C. Jones, M. P. Hayes, P. Yalamanchili, D. S. Casebier, Org. Lett. 2007, 9, 5617-5620.
40. P. D. O'Shea, D. Gauvreau, F. Gosselin, G. Hughes, C. Nadeau, A. Roy, C. S. Schultz, J. Org. Chem. 2009, 79, 4547-4553
41. C. G. Savarin, J. Chung, J. A. Murry, R. J. Cvetovich, C. McWilliams, D. Hughes, J. Amato, G. Boice, K. Conrad, E. Corley, R. Reamer, L. DiMichele, in Process Chemistry in the Pharmaceutical Industry, Vol.2 (Eds.:, K. Gadamasetti, T. Braish,), CRC, Boca Raton, 2008, pp. 65-87
42. C. G. Savarin, G. N. Boice, J. A. Murry, E. Corley, L. DiMichele, D. Hughes, Org. Lett. 2006, 8, 3903-3906.
43. R. B. Boar, J. F. McGhie, M. Robinson, D. H. R. Barton, D. C. Horwell, R. V. Stick, J. Chem. Soc. Perkin Trans. 1 1975, 1237-1241
44. R. B. Boar, J. F. McGhie, M. Robinson, D. H. R. Barton, J. Chem. Soc. Perkin Trans. 1 1975, 1242-1244.
45. D. H. R. Barton, S. Z. Zard, J. Chem. Soc. Perkin Trans. 1 1985, 2191-2192
46. M. J. Burk, G. Casy, N. B. Johnson, J. Org. Chem. 1998, 63, 6084-6085
47. G. Zhu, A. L. Casalnuovo, X. Zhang, J. Org. Chem. 1998, 63, 8100-8101
48. H. Zhao, C. P. Vandenbossche, S. G. Koenig, S. P. Singh, R. P. Bakale, Org. Lett. 2008, 10, 505-507
49. W. Tang, A. Capacci, M. Sarvestani, X. Wei, N. K. Yee, C. H. Senanayake, J. Org. Chem. 2009, 74, 9528-9530
50. Z.-H. Guan, K. Huang, S. Yu, X. Zhang, Org. Lett. 2009, 11, 481-484
51. Z.-H. Guan, Z.-Y. Zhang, Z.-H. Ren, Y.-Y. Wang, X. Zhang, J. Org. Chem. 2011, 76, 339-341.
52. As organoborane adducts:, G. M. Chen, H. C. Brown, J. Am. Chem. Soc. 2000, 122, 4217-4218
53. As HCl salts:, G. Hou, F. Gosselin, W. Li, J. C. McWilliams, Y. Sun, M. Weisel, P. D. O'Shea, C. Chen, I. W. Davies, X. Zhang, J. Am. Chem. Soc. 2009, 131, 9882-9883
54. D. R. Boyd, K. M. McCombe, N. D. Sharma, Tetrahedron Lett. 1982, 23, 2907-2908
55. P. L. Pickard, T. L. Tolbert, J. Org. Chem. 1961, 26, 4886-4888
56. P. L. Pickard, D. J. Vaughan, J. Am. Chem. Soc. 1950, 72, 876-878
57. P. L. Pickard, D. J. Vaughan, J. Am. Chem. Soc. 1950, 72, 5017-5019
58. A. Hantzsch, F. Kraft, Ber. Dtsch. Chem. Ges. 1891, 24, 3511-3528.
59. R. J. Mattson, K. M. Pham, D. J. Leuck, K. A. Cowen, J. Org. Chem. 1990, 55, 2552-2554
60. G. Liu, D. A. Cogan, T. D. Owens, T. P. Tang, J. A. Ellman, J. Org. Chem. 1999, 64, 1278-1284
61. B. Miriyala, S. Bhattacharyya, J. S. Williamson, Tetrahedron 2004, 60, 1463-1471
62. T. C. Nugent, V. N. Wakchaure, A. K. Ghosh, R. R. Mohanty, Org. Lett. 2005, 7, 4967-4970
63. T. C. Nugent, R. Seemayer, Org. Process Res. Dev. 2006, 10, 142-148
64. T. C. Nugent, A. K. Ghosh, V. N. Wakchaure, R. R. Mohanty, Adv. Synth. Catal. 2006, 348, 1289-1299.
65. R. Kucznierz, J. Dickhaut, H. Leinert, W. VonderSaal, Synth. Commun. 1999, 29, 1617-1625
66. M. Guillaume, J. Cuypers, J. Dingenen, Org. Process Res. Dev. 2007, 11, 1079-1086
67. T. C. Nugent, in Process Chemistry in the Pharmaceutical Industry, Vol.2 (Eds.:, K. Gadamasetti, T. Braish,), CRC, Boca Raton, 2008, pp. 137-156.
68. [Ti(edte)], [Ti(edtp)] and related complexes have been synthesized, isolated, characterized and used as catalysts for the preparation of polyurethanes:, A. A. D. Tulloch, D. Jenkins, J. Atkinson, M. A. Kent, A. Cooper, (Johnson Matthey PLC, UK), WO 2008155569, 2008.
69. A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, R. D. Shah, J. Org. Chem. 1996, 61, 3849-3862
70. T. C. Nugent, A. K. Ghosh, V. N. Wakchaure, R. R. Mohanty, Adv. Synth. Catal. 2006, 348, 1289-1299.
71. C. Salmi, Y. Letourneux, J. M. Brunel, Lett. Org. Chem. 2006, 3, 396-401.
72. J. S. M. Samec, A. H. Ell, J. B. Aaberg, T. Privalov, L. Eriksson, J.-E. Baeckvall, J. Am. Chem. Soc. 2006, 128, 14293-14305
73. T. Saied, M. L. Benkhoud, K. Boujlel, Synth. Commun. 2002, 32, 225-233.
74. Examples of titanium complexes with covalently bound ketimide ligands
75. M. R. Collier, M. F. Lappert, J. McMeeking, Inorg. Nucl. Chem. Lett. 1971, 7, 689-694
76. M. Bochmann, L. M. Wilson, M. B. Hursthouse, M. Motevalli, Organometallics 1988, 7, 1148-1154.
77. H. Fric, U. Schubert, New J. Chem. 2005, 29, 232-236.
78. 2O were not successful, as it isomerized to 2. Compound 39 has been prepared by photodecarbonylation of an oxazolinone and underwent isomerization to 2 with base:, A. Padwa, M. Akiba, L. A. Cohen, J. G. MacDonald, J. Org. Chem. 1983, 48, 695-703.