Alkyl, unsaturated, (hetero)aryl, and N-protected α-amino ketones by acylation of organometallic reagents

Journal of Organic Chemistry

Volumn 71, Issue 26, 2006, Pages 9861-9864

  Katritzky, Alan R ^a   Le, Khanh N B ^a   Khelashvili, Levan ^a   Mohapatra, Prabhu P ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLBENZOTRIAZOLES; AMINO KETONES; HETEROARYLLITHIUM; REAGENTS;

ACYLATION; AMINO ACIDS; CARBOXYLIC ACIDS; ORGANOMETALLICS; REACTION KINETICS; UNSATURATED COMPOUNDS;

KETONES;

ALKYL GROUP; ALPHA AMINO KETONE; AMINE; GRIGNARD REAGENT; KETONE DERIVATIVE; LITHIUM; N ACYLBENZOTRIAZOLE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DECOMPOSITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; TEMPERATURE SENSITIVITY;

EID: 33845963912     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0614801     Document Type: Article

References (51)

1. Katritzky, A. R.; Suzuki, K.; Wang, Z. Synlett 2005, 1656.
2. (a) Katritzky, A. R.; Zhang, Y.; Singh, S. K. Synthesis 2003, 2795.
3. (b) Katritzky, A. R.; Meher, N. K.; Cai, C.; Singh, S. K. Rev. Soc. Quim. Mex. 2004, 48, 275.
4. Katritzky, A. R.; He, H.-Y.; Suzuki, K. J. Org. Chem. 2000, 65, 8210.
5. Katritzky, A. R.; Yang, H.; Zhang, S.; Wang, M. ARKIVOC 2002, XI, 39.
6. Katritzky, A. R.; Pastor, A.; Voronkov, M. V. J. Heterocycl. Chem. 1999, 36, 111.
7. (a) Katritzky, A. R.; Pastor, A. J. Org. Chem. 2000, 65, 3679.
8. (b) Katritzky, A. R.; Jiang, R.; Suzuki, K. J. Org. Chem. 2005, 70, 4993.
9. (c) Katritzky, A. R.; Meher, N. K.; Singh, S. K. J. Org. Chem. 2005, 70, 7792.
10. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 1443.
11. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Wang, M. J. Org. Chem. 2003, 68, 4932.
12. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Akhmedova, R. G. ARKIVOC 2005, 329.
13. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Gromova, A. V.; Witek, R.; Steel, P. J. J. Org. Chem. 2005, 70, 9211.
14. Caprio, V. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: New York, 2005; p 135.
15. (a) Katritzky, A. R.; Suzuki, K.; Singh, S. K. Synthesis 2004, 2645.
16. (b) Katritzky, A. R.; Angrish, P.; Hür, D.; Suzuki, K. Synthesis 2005, 398.
17. (c) Katritzky, A. R.; Angrish, P.; Suzuki, K. Synthesis 2006, 411.
18. (a) Jorgenson, M. J. Org. React. 1970, 18, 1.
19. (b) Suga, K.; Watanabe, S.; Yamaguchi, Y.; Tohyama, M. Synthesis 1970, 189.
20. (c) Watanabe, S.; Suga, K.; Fujita, T.; Saito, N. Aust. J. Chem. 1977, 30, 427.
21. (a) Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964.
22. (b) Hansford, K. A.; Dettwiler, J. E.; Lubell, W. D. Org. Lett. 2003, 5, 4887.
23. (c) Dieter, R. K. Tetrahedron 1999, 55, 4177.
24. (d) Shirley, D. A. In Organic Reactions; Wiley: New York, 1954; Vol. 8, p 28.
25. (e) Lauer, D.; Staab, H. A. Chem. Ber. 1969, 102, 1631.
26. (f) Staab, H.; Jost, E. Ann. 1962, 655, 90.
27. (g) Kuhn, R.; Staab, H. A. Chem. Ber. 1954, 87, 262.
28. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
29. Mattson, M. N.; Rapoport, H. J. Org. Chem. 1996, 61, 6071.
30. (a) Knudsen, C. G.; Rapoport, H. J. Org. Chem. 1983, 48, 2260.
31. (b) Maurer, P. J.; Takahata, H.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 1095.
32. Lubell, W. D.; Rapoport, J. Org. Chem. 1989, 54, 3824.
33. Lubell, W. D.; Jamison, T. F.; Rapoport, H. J. Org. Chem. 1990, 55, 3511.
34. Wang, X.-J.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593.
35. (a) Cardelicchio, C.; Flandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Lett. 1987, 28, 2053.
36. (b) Malanga, C.; Aronica, L. A.; Lardicci, L. Tetrahedron Lett. 1995, 36, 9185.
37. Aldabbagh, F. Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier: New York, 2005; Vol. 5, p 1.
38. (a) Fristad, W. E.; Dime, D. S.; Bailey, T. R.; Paquette, L. A. Tetrahedron Lett. 1979, 20, 1999.
39. (b) Paquette, L. A.; Fristad, W. E.; Dime, D. S.; Bailey, T. R. J. Org. Chem. 1980, 45, 3017.
40. Gross, M.; Meienhofer, J. The Peptides; Academic Press: New York, 1979.
41. (a) Graham, S. L.; Scholz, T. H. Tetrahedron Lett. 1990, 31, 6269.
42. (b) Graham, S. L.; Scholz, T. H. J. Org. Chem. 1991, 56, 4260.
43. Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1988, 53, 2367.
44. Katritzky, A. R.; Singh, S. K.; Cai, C.; Bobrov, S. J. Org. Chem. 2006, 71, 3364.
45. Herbert, J. M.; Maggiani, M. Synth. Commun. 2001, 31, 947.
46. El-Khagawa, A. M.; El-Zohry, M. F.; Ismail, M. T. Phosphorous Sulfur 1987, 33, 25.
47. (a) Buckley, T. F., III; Rapoport, H. J. Am. Chem. Soc. 1981, 103, 6157.
48. (b) McClure, D. E.; Arison, B. H.; Jones, J. H.; Baldwin, J. J. J. Org. Chem. 1981, 46, 2431.
49. (c) Nordlander, J. E.; Payne, M. J.; Njoroge, F. G.; Balk, M. A.; Laikos, G. D.; Vishwanath, V. M. J. Org. Chem. 1984, 49, 4107.
50. (d) Nordlander, J. E.; Njoroge, F. G.; Payne, M. J.; Warman, D. J. Org. Chem. 1985, 50, 3481.
51. (e) Di Gioia, M. L.; Leggio, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. J. Org. Chem. 2001, 66, 7002.