Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Palladium-Catalyzed Asymmetric Allylic Alkylation in the Presence of Chiral Cinchonidinium Salts

키랄 신코니딘늄 염 존재 하에서 팔라듐-촉매 비대칭 알릴 알킬화 반응

  • Published : 2008.12.20
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Abstract

Keywords

EXPERIMENTAL

General procedure for the Pd-catalyzed enantioselective allylic alkylation of malonates 2

To a solution of [Pd(η3-C3H5)Cl]2 (0.9 mg, 0.0025 mmol), n-tributyl phosphine (1 mL, 0.005 mmol), and rac-1,3-diphenyl-2-enyl acetate (1, 25.2 mg, 0.1 mmol) in mesitylene (0.5 mL) were successively added Rb2CO3 (184.7 mg, 0.8 mmol), chiral ammonium salt VIII (6.1 mg, 0.01 mmol), and malonate (2, 0.2 mmol) at room temperature. After being stirred vigorously for 48 h, the reaction mixture was diluted with ethyl acetate (20 mL). The organic phase was washed with water (2 × 10 mL) and brine (10 mL). The extract was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate : benzene : hexane = 1:1:12) to give alkylated products 3.

References

  1. Tsuji, J. Palladium Reagents and Catalysis, Innovations in Organic Synthesis, Wiley, New York, 1995
  2. Trost, B. M.; van Varanken, D. L. Chem. Rev. 1996, 96, 395 https://doi.org/10.1021/cr9409804
  3. Trost, B. M.; Crawley, M. L. Chem. Rev. 2003, 103, 2921 https://doi.org/10.1021/cr020027w
  4. Trost, B. M.; Machacek, M. R.; Aponick, A. Acc. Chem. Res. 2006, 39, 747 https://doi.org/10.1021/ar040063c
  5. Pamies, O.; Dieguez, M.; Claver, C. Adv. Synth. Catal. 2007, 349, 836 https://doi.org/10.1002/adsc.200600489
  6. Inamoto, T.; Nishimura, M.; Koida, A.; Yoshida, K. J. Org. Chem. 2007, 72, 7413 https://doi.org/10.1021/jo071192k
  7. Bandini, M.; Melucci, M.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. Chem. Commun. 2007, 4519
  8. Dehmlow, E. V.; Dehmlow, S. S. 'Phase Transfer Catalysis', 3rd Ed., VCH, Weinheim, 1993
  9. Goldberg, Y. 'Phase Transfer Catalysis: Selected Problems and Application', Gordon & Breach Science Publ., Reading, 1992
  10. Starks, C. M.; Liotta, C. L.; Halpern, M. 'Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives', Chapman & Hall, New York, 1994
  11. Shioiri, T. 'Chiral Phase Transfer Catalysis', Chapter 14 in Handbook of Phase Transfer Catalysis, Sasson, Y., Neumann, R. (eds), Blackie Academic & Professional, London, 1997
  12. Nelson, A. Angew. Chem., Intl. Ed. Engl. 1999, 38, 1583 https://doi.org/10.1002/(SICI)1521-3773(19990601)38:11<1583::AID-ANIE1583>3.0.CO;2-E
  13. Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5655
  14. O'Donnell, M. J.; Delgado, F.; Hostettler, C.; Schwesinger, R. Tetrahedron Lett. 1998, 39, 8775 https://doi.org/10.1016/S0040-4039(98)01995-9
  15. Arai, S.; Oku, M.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 6785 https://doi.org/10.1016/S0040-4039(99)01282-4
  16. Arai, S.; Shirai, Y.; Ishida, T.; Shioiri, T. Tetrahedron 1999, 55, 6375 https://doi.org/10.1016/S0040-4020(99)00213-6
  17. Perrard, T.; Plaquevent, J. -C.; Desmurs, J-R.; Hebrault, D. Org. Lett. 2000, 2, 2956
  18. Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518 https://doi.org/10.1021/ar030058t
  19. O'Donnel, M. L. Acc. Chem. Res. 2004, 37, 506 https://doi.org/10.1021/ar0300625
  20. Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119,12414 https://doi.org/10.1021/ja973174y
  21. Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000 https://doi.org/10.1021/ja9835739
  22. Zhang, F. -Y; Corey, E. J. Org. Lett. 2000, 2, 1097 https://doi.org/10.1021/ol0056527
  23. Corey, E. J.; Zhang, F. -Y. Angew. Chem., Intl. Ed. Engl. 1999, 38, 1931 https://doi.org/10.1002/(SICI)1521-3773(19990712)38:13/14<1931::AID-ANIE1931>3.0.CO;2-4
  24. Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595 https://doi.org/10.1016/S0040-4039(97)10293-3
  25. Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 8671 https://doi.org/10.1016/S0040-4039(99)01836-5
  26. Nakoji, M.; Kanayama, T.; Okino, T.; Takemoto, Y. J. Org. Chem. 2002, 67, 7418 https://doi.org/10.1021/jo0260645
  27. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309 https://doi.org/10.1021/ol050413a
  28. Kim, H. R. Kim, D. Y. Tetrahedron Lett. 2005, 46, 3115 https://doi.org/10.1016/j.tetlet.2005.02.164
  29. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565 https://doi.org/10.1016/j.tetlet.2006.05.003
  30. Kang, Y. K.; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135
  31. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821
  32. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527 https://doi.org/10.1016/j.tetlet.2008.07.041
  33. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299 https://doi.org/10.1016/S0040-4039(01)01237-0
  34. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933 https://doi.org/10.1016/S0040-4020(01)00891-2
  35. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545 https://doi.org/10.1021/ol010281v
  36. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897 https://doi.org/10.1021/jo0401772
  37. Cho, M. G.; Cho, M. K.; Huh, S. C.; Kim, S. M.; Lee, K.; Koh, K. O.; Mang, J. Y.; Kim, D. Y. Bull. Korean Chem. Soc. 2006, 27, 857 https://doi.org/10.5012/bkcs.2006.27.6.857
  38. Inamoto, T.; Nishimura, M.; Koida, A.; Yoshida, K. J. Org. Chem. 2007, 72, 7413 https://doi.org/10.1021/jo071192k
  39. Glegola, K.; Framery, E.; Goux-Henry, C.; Pietrusiewicz, K. M.; Sinou, D. Tetrahedron 2007, 63, 7133 https://doi.org/10.1016/j.tet.2007.04.098
  40. Feng, J.; Bohle, D. S.; Li, C.-J. Tetrahedron: Asymmertry 2007, 18, 1043 https://doi.org/10.1016/j.tetasy.2007.05.005

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