Enantioselective Michael Reaction of Fluoromalonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt

Bulletin of the Korean Chemical Society

Volumn 24, Issue 10, 2003, Pages 1425-1426

  Kim, Dae Young ^a   Kim, Sung Min ^a   Koh, Kwang Oh ^a   Mang, Joo Yang ^a   Lee, Kilsung ^b  

^a Soonchunhyang University   (South Korea)

^b Cheil Industries Inc   (South Korea)

Author keywords

Ammonium salt; Asymmetric reactions; Michael reactions; Phase transfer catalyst

Indexed keywords

CHALCONE; FLUOROMALONATE DERIVATIVE; MALONIC ACID DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; MICHAEL ADDITION; PHASE TRANSFER CATALYSIS;

EID: 0348049553     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2003.24.10.1425     Document Type: Article

References (36)

1. For recent reviews and monographs, see: (a) Leonard, J. Contemp. Org. Synth. 1994, 1, 387.
2. (b) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon: Oxford, 1992.
3. (c) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
4. (a) Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1996, 35, 104.
5. (b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506.
6. (c) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
7. (d) Hanessian, S.; Pham, V. Org. Lett. 2000, 2, 2975.
8. (e) Narasimhan, S.; Balakumar, V. R.; Radhakrishnan, V. Tetrahedron Lett. 2001, 42, 719.
9. (f) Sundarajan, G.; Prabagaran, N. Org. Lett. 2001, 3, 389.
10. (g) Perrard, T.; Plaquevent, L.-C.; Desmurs, J.-R.; Hebrault, D. Org. Lett. 2000, 2, 2959.
11. (a) Dehmlow, E. V. and S. S. Phase Transfer Catalysis, 3rd Ed.; VCH: Weinheim, 1993.
12. (b) Goldberg, Y. Phase Transfer Catalysis: Selected Problems and Application; Gordon & Breach Science Publ.: Reading, 1992.
13. (c) Starks, C. M.; Liotta, C. L.; Halpern, M. Phase Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Chapman & Hall: New York, 1994.
14. (d) Shioiri, T. Chiral Phase Transfer Catalysis, Chapter 14 in Handbook of Phase Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Blackie Academic & Professional: London, 1997.
15. (e) O'Donnell, M. J. Asymmetric Phase Transfer Reactions, Chapter 10 in Catalytic Asymmetric Synthesis; Ojima, I., Eds.; Wiley-VCH: 2000.
16. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414.
17. (b) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000.
18. (c) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347.
19. (d) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 39, 3843.
20. (e) Corey, E. J.; Zhang, F.-Y. Org. Lett 1999, 1, 1287.
21. (f) Zhang, F.-Y; Corey, E. J. Org. Lett. 2000, 2, 1097.
22. (g) Corey, E. J.; Zhang, F.-Y. Angew. Chem., Intl. Ed. 1999, 38, 1931.
23. (h) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595.
24. (i) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599.
25. (j) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 8671.
26. (k) Lygo, B.; Wainwright, P. G. Tetrahedron 1999, 55, 6289.
27. (l) Oku, M.; Arai, S.; Katayama, K.; Shioiri, T. Synlett 2000, 493.
28. (m) Arai, S., Shirai, Y.; Ishida, T.; Shioiri, T. Tetrahedron 1999, 55, 6375.
29. (n) Arai, S.; Hamaguchi, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2997.
30. (o) Park, H.-g.; Jeong, B.-s.; Yoo, M.-s.; Lee, J.-h.; Park, B.-s.; Kim, M. G.; Jew, S.-s. Tetrahedron Lett. 2003, 44, 3497.
31. (p) Jew, S.-s.; Yoo, M.-s.; Jeong, B.-s.; Park, I. Y.; Park, H.-g. Org. Lett. 2002, 4, 4245.
32. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545.
33. (a) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
34. (b) Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933.
35. (c) 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.
36. 4, filtered, concentrated, and purified by flash chromatography (silica gel, ethyl acetate: hexane = 1: 6) to afford Michael adduct 3.