Chiral N-phosphonyl imine chemistry: Asymmetric addition of ketone-derived enolates for the synthesis of β-amino ketones

Synthesis

Volumn , Issue 16, 2008, Pages 2519-2526

  Han, Jianlin ^a   Ai, Teng ^a   Li, Guigen ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

amino ketone; C2 symmetric diamine; N phosphonyl imine; Phosphoramide

Indexed keywords

ADDITION REACTIONS; AMINATION; AMINES; CATALYST ACTIVITY; CHEMICAL REACTIONS; LITHIUM; METHANOL; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

ASYMMETRIC ADDITION; C2- SYMMETRIC DIAMINE; N-PHOSPHONYL IMINE; PHOSPHORAMIDE;

KETONES;

BENZYL DERIVATIVE; BROMINE DERIVATIVE; IMINE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; METHANOL; NAPHTHYL GROUP;

ADDITION REACTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; DIASTEREOISOMER; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY;

EID: 47949123464     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067189     Document Type: Article

References (37)

1. (a) Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069.
2. (b) Cheng, R. P.; Gellman, S. H.; Degrado, W. F. Chem. Rev. 2001, 101, 3219.
3. (a) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
4. (b) Seebach, D.; Kimmerlin, T.; Sebesta, R.; Campo, M. A.; Beck, A. K. Tetrahedron 2004, 60, 7455.
5. (a) Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2003, 125, 11276.
6. (b) Enders, D.; Moser, M.; Geibel, G.; Laufer, M. C. Synthesis 2004, 2040.
7. (a) Cordova, A. Acc. Chem. Res. 2004, 37, 102.
8. (b) Juhl, K.; Gathergood, N.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2001, 40, 2995.
9. (c) Trost, B. M.; Terrell, L. R. J. Am. Chem. Soc. 2003, 125, 338.
10. (d) Matsunaga, S.; Kumagai, N.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 4712.
11. (e) Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem. Int. Ed. 2005, 44, 1525.
12. (f) Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048.
13. (g) Cordova, A.; Notz, W.; Zhong, G.; Betancort, J. M.; Barbas, C. F. III J. Am. Chem. Soc. 2002, 124, 1842.
14. (h) Kano, T.; Yamaguchi, Y.; Tokuda, O.; Maruoka, K. J. Am. Chem. Soc. 2005, 127, 16408.
15. (i) Ramasastry, S. S. V.; Zhang, H.; Tanaka, F.; Barbas, C. F. III J. Am. Chem. Soc. 2007, 129, 288.
16. Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044.
17. (a) Josephsohn, N. S.; Carswell, E. L.; Snapper, M. L.; Hoveyda, A. H. Org. Lett. 2005, 7, 2711.
18. (b) Ibrahem, I.; Cordova, A. Tetrahedron Lett. 2005, 46, 2839.
19. (c) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
20. (d) Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizume, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435.
21. (e) Notz, W.; Watanabe, S.; Chowdari, N. S.; Zhong, G.; Betancort, J. M.; Tanaka, F.; Barbas, C. F. III Adv. Synth. Catal. 2004, 346, 1131.
22. (f) Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
23. Davis, F. A.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13.
24. Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
25. (a) Xu, X.; Liu, Y.; Chen, D.; Timmons, C.; Li, G. Eur. J. Org. Chem. 2005, 1805.
26. (b) Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356.
27. (c) Davis, F. A.; Yang, B. J. Am. Chem. Soc. 2005, 127, 8398.
28. (d) Gridnev, I. D.; Kouchi, M.; Sorimachi, K.; Terada, M. Tetrahedron Lett. 2007, 48, 497.
29. (a) Terada, M.; Machioka, K.; Sorimachi, K. Angew. Chem. Int. Ed. 2006, 45, 2254.
30. (b) Connon, S. J. Angew. Chem. Int. Ed. 2006, 45, 3909.
31. (c) Lanter, J. C.; Chen, H. F.; Zhang, X. Q.; Sui, Z. H. Org. Lett. 2005, 7, 5905.
32. Nakamura, Y.; Matsubara, R.; Kiyohara, H.; Kobayashi, S. Org. Lett. 2003, 5, 2481.
33. (a) Kattuboina, A.; Li, G. Tetrahedron Lett. 2008, 49, 1573.
34. (b) Kattuboina, A.; Kaur, P.; Ai, T.; Li, G. Chem. Biol. Drug Des. 2008, 216.
35. (a) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12.
36. (b) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722.
37. Tillman, A. L.; Dixon, D. J. Org. Biomol. Chem. 2007, 5, 606.