Organocatalytic enantioselective synthesis of tertiary α-hydroxy phosphonates

Bulletin of the Korean Chemical Society

Volumn 32, Issue 3, 2011, Pages 785-786

  Lee, Hyun Joo ^a   Kim, Ji Hyeon ^b   Kim, Dae Young ^a  

^a Soonchunhyang University   (South Korea)

^b Gachon University   (South Korea)

Author keywords

Hydroxy phosphonates; Keto phosphonates; Aldol reaction; Enamine catalysis

Indexed keywords

EID: 79953247417     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.3.785     Document Type: Article

References (52)

1. For a review that includes synthesis of a-hydroxy phosphonates, see: Wiemer, D. F. Tetrahedron 1997, 53, 16609.
2. Kolodiazhnyi, O. I. Tetrahedron: Asymmetrty 2005, 16, 3295.
3. Merino, P.; Marques-Lopez, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195.
4. Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Biochemistry 1992, 31, 3800.
5. Hohl, R. J.; Lewis, K. A.; Cermak, D. M.; Wiemer, D. F. Lipids 1998, 33, 39.
6. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591.
7. Stowasser, B.; Budt, K. H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625.
8. Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han, C. Y.; Lin, K. C.; Pansegrau, P. D.; Ream, J. E.; Schnur, D.; Shah, A.; Walker, M. C. Phosphorus Sulfur Silicon Relat. Elem. 1993, 76, 115.
9. McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131.
10. Hammerschmidt, F.; Schmidt, S. Eur. J. Org. Chem. 2000, 2239.
11. Kim, D. Y.; Wiemer, D. F. Tetrahedron Lett. 2003, 44, 2803.
12. Zhou, X.; Liu, Y.; Zhao, J.; Shang, D.; Liu, X.; Lin, L.; Feng, X. Adv. Synth. Catal. 2009, 351, 2567.
13. Samanta, S.; Zhao, C. G. J. Am. Chem. Soc. 2006, 128, 7442.
14. Liu, J.; Yang, Z. G.; Wang, Z.; Wang, F.; Chen, X. H.; Liu, X. H.; Feng, X. M.; Su, Z. S.; Hu, C. W. J. Am. Chem. Soc. 2008, 130, 5654.
15. Huang, J. L.; Wang, J.; Chen, X. H.; Wen, Y. H.; Liu, X. H.; Feng, X. M. Adv. Synth. Catal. 2008, 350, 287.
16. Chen, X. H.; Wang, J.; Zhu, Y.; Shang, D. J.; Gao, B.; Liu, X. H.; Feng, X. M.; Su, Z. S.; Hu, C. W. Chem-Eur. J. 2008, 14, 10896.
17. Mandal, T.; Samanta, S.; Zhao, C. G. Org. Lett. 2007, 9, 943.
18. Gondi, V. B.; Hagihara, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2009, 48, 776.
19. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
20. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933.
21. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
22. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897.
23. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309.
24. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565.
25. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
26. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
27. Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2093
28. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036.
29. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036.
30. Mang, J. Y.; Whang, I. S.; Kwon, D. G.; Kim, D. Y. J. Korean Chem. Soc. 2008, 52, 724.
31. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259.
32. Kang, S. H.; Kang, Y. K.; Kim, D. Y. Tetrahedron 2009, 65, 5676.
33. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249.
34. Lee, N. R.; Kim, S. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829.
35. Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1437.
36. Kang, S. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1439.
37. Kwon, B. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1441.
38. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917.
39. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783.
40. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847.
41. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
42. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527.
43. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734.
44. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779.
45. Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759.
46. Oh, Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674.
47. Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896.
48. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734.
49. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779.
50. Lee, J. H.; Kim, D. Y. Synthesis 2010, 1860.
51. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906.
52. General procedure for asymmetric synthesis of a-hydroxy alkylphosphonates 3: To a stirred solution of a-keto phosphonate (1, 0.3 mmol), 4-nitrobenzoic acid (5.0 mg, 0.03 mmol), and catalyst I (5.8 mg, 0.015 mmol) in THF (0.7 mL) was added acetone (0.66 mL, 9 mmol). Reaction mixture was stirred for 4-15 h at room temperature, concentrated, and purified by flash column chromatography (EtOAc) to afford the aldol product 3.