Importance of chiral phase-transfer catalysts with dual functions in obtaining high enantioselectivity in the Michael reaction of malonates and chalcone derivatives

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3195-3197

  Ooi, Takashi ^a   Ohara, Daisuke ^a   Fukumoto, Kazuhiro ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

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EID: 23044474944     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050902a     Document Type: Article

References (33)

1. For recent reviews, see: (a) Shioiri, T. In Handbook of Phase-Transfer Catalysis; Sasson, Y., Neumann, R., Eds.; Blackie Academic & Professional: London, 1997; Chapter 14.
2. (b) Shioiri T.; Arai, S. In Stimulating Concepts in Chemistry, Vogtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p 123.
3. (c) O'Donnell, M. J. In Catalytic Asymmetric Syntheses, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000; Chapter 10.
4. (d) O'Donnell, M. J. Aldrichimica Acta 2001, 34, 3.
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7. (g) Lygo, B.; Andrews, B. I. Acc. Chem. Res. 2004, 37, 518.
8. Recent representative examples of phase-transfer-catalyzed asymmetric epoxidation: (a) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599.
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16. (i) Jew, S.-s.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.; Kim, M.-J.; Lee, Y.-J.; Lee, J.; Choi, S.-h.; Lee, K.; Lah, M. S.; Park, H.-g. Angew. Chem., Int. Ed. 2005, 44, 1383.
17. Asymmetric dihydroxylation: Bhunnoo, R. A.; Hu, Y.; Lainé, D. I.; Brown, R. C. D. Angew. Chem., Int. Ed. 2002, 41, 3479.
18. See also: Brown, R. C. D.; Keily, J. F. Angew. Chem., Int. Ed. 2001, 40, 4496.
19. For other contributions, see, for example: (a) Asymmetric Michael addition of 2-nitropropane: Bakó, P.; Czinege, E.; Bakó, T.; Czugler, M.; Tõke, L. Tetrahedron: Asymmetry 1999, 10, 4539.
20. (b) Asymmetric cyclopropanation: Arai, S.; Nakayama, K.; Ishida, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4215.
21. (c) Asymmetric aldol reaction: Arai, S.; Hasegawa, K.; Nishida, A. Tetrahedron Lett. 2004, 45, 1023. See also ref 1c.
22. (a) Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299.
23. (b) Dere, R. T.; Pal, R. R.; Patil, P. S.; Salunkhe, M. M. Tetrahedron Lett. 2003, 44, 5351.
24. See also: (c) Loupy, A.; Zaparucha, A. Tetrahedron Lett. 1993, 34, 473.
25. For the asymmetric Michael addition of malonates to chalcone catalyzed by chiral metal complexes, see: (a) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
26. (b) Kumaraswamy, G.; Sastry, M. N. V.; Jena, N. Tetrahedron Lett. 2001, 42, 8515.
27. Ooi, T.; Ohara, D.; Tamura, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 6844.
28. 3, R = H).
29. Present method could not be extended well to aliphatic enones. For example, the reaction of diethyl malonate with trans-4-phenyl-3-buten-2-one under the influence of 1 proceeded slowly at 0°C to furnish the desired Michael adduct in 98% yield with 8% ee after 96 h.
30. For catalytic asymmetric Michael addition of malononitrile to α,β-unsaturated ketones, see: (a) Taylor, M. S.; Zalatan, D. N.; Lerchner, A. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2005, 127, 1313.
31. For related studies, see: (b) Itoh, K.; Oderaotoshi, Y.; Kanemasa, S. Tetrahedron: Asymmetry 2003, 14, 635.
32. (c) Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 11204.
33. Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1996, 37, 6343.