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Organocatalytic Enantioselective Synthesis of Tertiary α-Hydroxy Phosphonates

  • Lee, Hyun-Joo (Department of Chemistry, Soonchunhyang University) ;
  • Kim, Ji-Hyeon (Department of Chemical and Bio Engineering, Kyungwon University) ;
  • Kim, Dae-Young (Department of Chemistry, Soonchunhyang University)
  • Received : 2010.12.25
  • Accepted : 2011.01.12
  • Published : 2011.03.20

Abstract

Keywords

References

  1. Wiemer, D. F. Tetrahedron 1997, 53, 16609. https://doi.org/10.1016/S0040-4020(97)10305-2
  2. Kolodiazhnyi, O. I. Tetrahedron: Asymmetrty 2005, 16, 3295. https://doi.org/10.1016/j.tetasy.2005.09.007
  3. Merino, P.; Marques-Lopez, E.; Herrera, R. P. Adv. Synth. Catal. 2008, 350, 1195. https://doi.org/10.1002/adsc.200800131
  4. Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Biochemistry 1992, 31, 3800. https://doi.org/10.1021/bi00130a010
  5. Hohl, R. J.; Lewis, K. A.; Cermak, D. M.; Wiemer, D. F. Lipids 1998, 33, 39. https://doi.org/10.1007/s11745-998-0178-x
  6. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591. https://doi.org/10.1016/S0040-4039(00)97904-8
  7. Stowasser, B.; Budt, K. H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625. https://doi.org/10.1016/S0040-4039(00)61002-X
  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. https://doi.org/10.1080/10426509308032372
  9. McEldoon, W. L.; Wiemer, D. F. Tetrahedron 1995, 51, 7131. https://doi.org/10.1016/0040-4020(95)00363-D
  10. Hammerschmidt, F.; Schmidt, S. Eur. J. Org. Chem. 2000, 2239.
  11. Kim, D. Y.; Wiemer, D. F. Tetrahedron Lett. 2003, 44, 2803. https://doi.org/10.1016/S0040-4039(03)00454-4
  12. Zhou, X.; Liu, Y.; Zhao, J.; Shang, D.; Liu, X.; Lin, L.; Feng, X. Adv. Synth. Catal. 2009, 351, 2567. https://doi.org/10.1002/adsc.200900531
  13. Samanta, S.; Zhao, C. G. J. Am. Chem. Soc. 2006, 128, 7442. https://doi.org/10.1021/ja062091r
  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. https://doi.org/10.1021/ja800839w
  15. Huang, J. L.; Wang, J.; Chen, X. H.; Wen, Y. H.; Liu, X. H.; Feng, X. M. Adv. Synth. Catal. 2008, 350, 287. https://doi.org/10.1002/adsc.200700392
  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. https://doi.org/10.1002/chem.200801958
  17. Mandal, T.; Samanta, S.; Zhao, C. G. Org. Lett. 2007, 9, 943. https://doi.org/10.1021/ol070209i
  18. Gondi, V. B.; Hagihara, K.; Rawal, V. H. Angew. Chem., Int. Ed. 2009, 48, 776. https://doi.org/10.1002/anie.200804244
  19. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299. https://doi.org/10.1016/S0040-4039(01)01237-0
  20. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933. https://doi.org/10.1016/S0040-4020(01)00891-2
  21. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  22. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897. https://doi.org/10.1021/jo0401772
  23. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309. https://doi.org/10.1021/ol050413a
  24. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565. https://doi.org/10.1016/j.tetlet.2006.05.003
  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 https://doi.org/10.5012/bkcs.2008.29.11.2093
  28. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036. https://doi.org/10.5012/bkcs.2008.29.10.2036
  29. Kim, D. Y. Bull. Korean Chem. Soc. 2008, 29, 2036. https://doi.org/10.5012/bkcs.2008.29.10.2036
  30. Mang, J. Y.; Whang, I. S.; Kwon, D. G.; Kim, D. Y. J. Korean Chem. Soc. 2008, 52, 724. https://doi.org/10.5012/jkcs.2008.52.6.724
  31. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259. https://doi.org/10.1016/j.jfluchem.2008.11.001
  32. Kang, S. H.; Kang, Y. K.; Kim, D. Y. Tetrahedron 2009, 65, 5676. https://doi.org/10.1016/j.tet.2009.05.037
  33. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 249. https://doi.org/10.5012/bkcs.2009.30.1.249
  34. Lee, N. R.; Kim, S. M.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 829. https://doi.org/10.5012/bkcs.2009.30.4.829
  35. Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1437. https://doi.org/10.5012/bkcs.2009.30.7.1437
  36. Kang, S. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1439. https://doi.org/10.5012/bkcs.2009.30.7.1439
  37. Kwon, B. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1441. https://doi.org/10.5012/bkcs.2009.30.7.1441
  38. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917. https://doi.org/10.2174/138527210791111768
  39. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783. https://doi.org/10.1002/adsc.201000515
  40. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847. https://doi.org/10.1021/ja103786c
  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. https://doi.org/10.1016/j.tetlet.2008.07.041
  43. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734. https://doi.org/10.1021/jo900880t
  44. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  45. Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759. https://doi.org/10.1016/j.jfluchem.2009.06.002
  46. Oh, Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674. https://doi.org/10.1016/j.tetlet.2009.06.003
  47. Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896. https://doi.org/10.1016/j.tetlet.2009.06.056
  48. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734. https://doi.org/10.1021/jo900880t
  49. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  50. Lee, J. H.; Kim, D. Y. Synthesis 2010, 1860.
  51. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906. https://doi.org/10.1016/j.tetlet.2010.03.105

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