Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Asymmetric Michael Reaction of Malonate Derivatives with α, β-Unsaturated Ketones

  • Published : 2006.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

The catalytic enantioselective Michael reaction promoted by quaternary ammonium salts from Cinchona alkaloids as a phase-transfer catalyst is described. Treatment of malonates with $\alpha$,$\beta$-unsaturated ketones under mild reaction conditions afforded the corresponding Michael adducts in good yields with good to moderate enantiomeric excesses.

Keywords

References

  1. Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed.; VCH: Weinheim, 1993
  2. Goldberg, Y. Phase Transfer Catalysis: Selected Problems and Application; Gordon & Breach Science, Reading: 1992
  3. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Chapman & Hall, New York, 1994
  4. Shioiri, T. In Handbook of Phase- Transfer Catalysis; Sasson, Y., Neumann. R., Eds.; Blackie Academic & Professional: London, 1997; Ch. 14
  5. Shioiri, T.; Arai, S. In Stimulating Concepts in Chemistry; Vogtle. F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p 123
  6. O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Ch. 10
  7. O'Donnell, M. J. Aldrichchimica Acta 2001, 34, 3
  8. Maruoka, K.; Ooi, T. Chem. Rev. 2003, 103, 3013 https://doi.org/10.1021/cr020020e
  9. O'Donnell, M. J. Acc. Chem. Res. 2004, 37, 506 https://doi.org/10.1021/ar0300625
  10. Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518 https://doi.org/10.1021/ar030058t
  11. Leonard, J. Contemp. Org. Synth. 1994, 1, 387 https://doi.org/10.1039/co9940100387
  12. Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992
  13. Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771 https://doi.org/10.1021/cr00013a002
  14. Dieter, R. K.; Alexander, C. W.; Nice, L. E. Tetrahedron 2000, 56, 2767 https://doi.org/10.1016/S0040-4020(00)00130-7
  15. Park, Y. S.; Weisenburger, G. A.; Beak, P. J. Am. Chem. Soc. 1997, 199, 10537
  16. Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109 https://doi.org/10.1021/jo00057a024
  17. Shawe, T. T.; Meyers, A. I. J. Org. Chem. 1991, 56, 2751 https://doi.org/10.1021/jo00008a033
  18. Patrocinio, V. L.; Costa, P. R. R.; Correia, C. R. D. Synthesis 1994, 474
  19. Sawamura, H.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295 https://doi.org/10.1021/ja00047a053
  20. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104 https://doi.org/10.1002/anie.199601041
  21. Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557 https://doi.org/10.1016/S0040-4039(98)01644-X
  22. Shimizu, S.; Ohori, K.; Arao, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547 https://doi.org/10.1021/jo981069g
  23. Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506 https://doi.org/10.1021/ja001036u
  24. Takita, R.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2002, 43, 4661 https://doi.org/10.1016/S0040-4039(02)00882-1
  25. Anamalai, V.; DiMauro, E. F.; Carroll, P. J.; Kozlowski, M. C. J. Org. Chem. 2003, 63, 1973
  26. Kumaraswamy, G.; Jena, N.; Sastrys, M. N. V.; Venkata Ras, G.; Ankamma, K. J. Mol. Cat. A 2005, 230, 39
  27. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Tetrahedron 1997, 53, 11223 https://doi.org/10.1016/S0040-4020(97)00379-7
  28. Yamaguchi, M.; Shiraishi, T.; Igarashi, Y.; Hirama, M. Tetrahedron Lett. 1994, 25, 823
  29. Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520 https://doi.org/10.1021/jo960216c
  30. Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975 https://doi.org/10.1021/ol000170g
  31. Narasimhan, S.; Balakumar, V. R.; Radhakrishnan, V. Tetrahedron Lett. 2001, 42, 719 https://doi.org/10.1016/S0040-4039(00)01986-9
  32. Sundarajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389 https://doi.org/10.1021/ol006898e
  33. DiMauro, E. F.; Kozlowski, M. C. Org. Lett. 2001, 3, 1641 https://doi.org/10.1021/ol0158213
  34. Jha, S. C.; Joshi, N. N. Tetrahedron: Asymmetry 2001, 12, 2463 https://doi.org/10.1016/S0957-4166(01)00433-5
  35. MacCulloch, A. C.; Yolka, S.; Jackson, R. F. W. Synlett 2002, 1700
  36. Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805 https://doi.org/10.1016/S0040-4039(00)78503-0
  37. Perrard, T.; Plaquevent, L.-C.; Desmurs, J.-R.; Hebrault, D. Org. Lett. 2000, 2, 2959 https://doi.org/10.1021/ol006207e
  38. Ooi, T.; Ohara, D.; Fukumoto, K.; Maruoka, K. Org. Lett. 2005, 7, 3195 https://doi.org/10.1021/ol050902a
  39. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933 https://doi.org/10.1016/S0040-4020(01)00891-2
  40. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545 https://doi.org/10.1021/ol010281v
  41. Kim, D. Y.; Choi, Y. J.; Park, H. Y.; Joung, C. U.; Koh, K. O.; Mang, J. Y.; Jung, K.-Y. Synth. Commun. 2003, 33, 435 https://doi.org/10.1081/SCC-120015774
  42. Park, E. J.; Kim, H. R.; Joung, C. W.; Kim, D. Y. Bull. Korean Chem. Soc. 2004, 25, 1451 https://doi.org/10.5012/bkcs.2004.25.10.1451
  43. Kim, D. Y.; Huh, S. C. Bull. Korean Chem. Soc. 2004, 25, 347 https://doi.org/10.5012/bkcs.2004.25.3.347
  44. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897 https://doi.org/10.1021/jo0401772
  45. Kim, H. R.; Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115 https://doi.org/10.1016/j.tetlet.2005.02.164
  46. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309 https://doi.org/10.1021/ol050413a
  47. Kim, S. M.; Kang, Y. K.; Lee, K.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 26, 423 https://doi.org/10.5012/bkcs.2006.27.3.423
  48. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565 https://doi.org/10.1016/j.tetlet.2006.05.003
  49. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299 https://doi.org/10.1016/S0040-4039(01)01237-0
  50. Kim, D. Y.; Kim, S. M.; Koh, K. O.; Mang, J. Y. Bull. Korean Chem. Soc. 2003, 24, 1425 https://doi.org/10.5012/bkcs.2003.24.10.1425
  51. Park, B. S.; Kim, D. Y.; Rosenthal, P. J.; Huh, S. C.; Lee, B. J.; Park, S. M.; Kim, J. E.; Kim, M. H.; Huh, T. L.; Choi, Y, J.; Suh, K. H.; Choi, W. S.; Lee, S. E. Bioorg. Med. Chem. Lett. 2002, 12, 1351 https://doi.org/10.1016/S0960-894X(02)00173-7
  52. Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu, M. Organofluorine Compounds: Chemistry and Applications; Springer-Verlag: Berlin, 2000
  53. Biomedical Frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, DC, 1996

Cited by

  1. Pharmacological significance of triazole scaffold vol.26, pp.1, 2011, https://doi.org/10.3109/14756360903524304
  2. Enantioselective Michael Addition Reactions vol.43, pp.1, 2011, https://doi.org/10.1080/00304948.2011.547102
  3. Organocatalytic Enantioselective Michael Addition of Silyl Malonate to α,β-Unsaturated Enones: One-pot Synthesis of Chiral δ-Keto Esters vol.34, pp.9, 2013, https://doi.org/10.5012/bkcs.2013.34.9.2569
  4. 2-Fluoromalonate Esters: Fluoroaliphatic Building Blocks for the Life Sciences vol.18, pp.8, 2014, https://doi.org/10.1021/op500141c
  5. Non-Covalent Immobilization of Rare Earth Heterobimetallic Frameworks and their Reactivity in an Asymmetric Michael Addition vol.356, pp.6, 2014, https://doi.org/10.1002/adsc.201400087
  6. Catalytic Enantioselective Desymmetrization of meso-Aziridines with Fluoromalonates vol.94, pp.7, 2017, https://doi.org/10.3987/COM-17-13725
  7. Asymmetric Michael Reaction of Malonate Derivatives with α,β-Unsaturated Ketones Using Chiral Quaternary Ammonium Salts. vol.37, pp.52, 2006, https://doi.org/10.1002/chin.200652030
  8. Selective difluoromethylation and monofluoromethylation reactions pp.48, 2009, https://doi.org/10.1039/b916463d
  9. Catalytic Asymmetric Fluorination of α-Chloro-β-ketoesters in the Presence of Chiral Palladium Complexes vol.28, pp.12, 2007, https://doi.org/10.5012/bkcs.2007.28.12.2191
  10. Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes vol.28, pp.12, 2006, https://doi.org/10.5012/bkcs.2007.28.12.2435
  11. One-Pot Synthesis of 1,2,3-Triazoles from Michael Reaction vol.29, pp.4, 2008, https://doi.org/10.5012/bkcs.2008.29.4.723
  12. Palladium-Catalyzed Asymmetric Allylic Alkylation in the Presence of Chiral Cinchonidinium Salts vol.52, pp.6, 2006, https://doi.org/10.5012/jkcs.2008.52.6.724
  13. Enantioselective Fluorination of β-Keto Phosphonates and β-Ketoesters Catalyzed by Chiral Palladium Complexes vol.30, pp.4, 2006, https://doi.org/10.5012/bkcs.2009.30.4.829
  14. Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester vol.10, pp.None, 2014, https://doi.org/10.3762/bjoc.10.119
  15. Enantioselective Michael Addition of Malonates to Enones vol.24, pp.None, 2020, https://doi.org/10.2174/1385272824666200316122221