A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates

Tetrahedron

Volumn 53, Issue 50, 1997, Pages 17015-17028

  Kitajima, Hiroshi ^a   Ito, Katsuji ^b   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b FUKUOKA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BUTENOLIDE; FURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030781212     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10152-1     Document Type: Article

References (57)

1. (a) Rao, Y.S. Chem. Rev. 1964, 64, 353-388.
2. (b) Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J. In Studies in Natural Products Chemistry; Atta-er-Rahman, Ed.; Vol. 3, Elsevier: Amsterdam, 1989; pp 157.
3. (a) Hanessian, S.; Murray, J. P.; Sahoo, P.S. Tetrahedron Lett. 1985, 26, 5627-5630.
4. (b) Hanessian, S.; Murray, J. P. Can. J. Chem. 1986, 64, 2231-2234.
5. (c) Hanessian, S.; Sahoo, P. S.; Botta, M. Tetrahedron Lett. 1987, 28, 1147-1150.
6. (d) Mattes, H.; Hamada, K.; Benezra, C. J. Med. Chem. 1987, 30, 1948-1951.
7. (e) Hanessian, S.; Cooke, G. N.; DeHoff, B.; Sakito, Y. J. Am. Chem. Soc. 1990, 112, 5276-5290.
8. (f) Pelter, A.; Al-Bayati, H. I. R.; Ayoub, T. M., Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742.
9. (g) de Lange, B.; van Bolhuis, F.; Feringa, B. L. Tetrahedron 1989, 45, 6799-6818.
10. (h) de Jong, J. C.; van Bolhuis, F.; Feringa, B. L. Tetrahedron: Asymmetry 1991, 2, 1247-1262.
11. (i) Pelter, A.; Ward, S. R.; Jones, M. D., Maddocks, P. J. Chem. Soc. Perkin Trans. 1 1993, 2621-2629.
12. (a) Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953-1956.
13. (b) Jefford, W. C.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044.
14. (a) Brown, W. D.; Campbell, M. M.; Taylor, P. A.; Zhang, X. Tetrahedron Lett. 1987, 28, 985-988.
15. (b) Jefford, W. C.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037-4040.
16. (c) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. Tetrahedron Lett. 1989, 30, 5325-5328.
17. (d) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri, F.; Belicchi, F. M. Tetrahedron 1990, 46, 5807-5824.
18. (e) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1990, 55, 2565-2567.
19. (f) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 2135-2139.
20. (g) Bauer, T. Tetrahedron: Asymmetry 1996, 7, 981-984.
21. (a) Harding, E. K.; Coleman, T. M.; Liu, T. L. Tetrahedron Lett. 1991, 32, 3795-3798.
22. (b) Martin, F. S.; Corbett, W. J. Synthesis 1992, 55-57.
23. (c) Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-5776.
24. (d) Pelter, A.; Ward, S. R.; Sirit, A. Tetrahedron: Asymmetry 1994, 5, 1745-1762.
25. (e) Martin, F. S.; Barr, J. K. J. Am. Chem. Soc. 1996, 118, 3299-3300.
26. (a) Camiletti, C.; Poletti, L.; Trombini, C. J. Org. Chem. 1994, 59, 6843-6846.
27. (b) Castellari, C.; Lombardo, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059-1068.
28. (a) Fukuyama, T.; Yang, L. Tetrahedron Lett. 1986, 27, 6299-6300.
29. (b) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1987, 709, 7881-7882.
30. (c) Fukuyama, T.; Yang, L. J. Am. Chem. Soc. 1989, 111, 8303-8304.
31. (d) Brimble, A. M.; Brimble, T. M.; Gibson, J. J. J. Chem. Soc. Perkin Trans. 1. 1989, 179-183.
32. (e) Brimble, A. M.; Duncalf, J. L.; Reid, C. W. D. Tetrahedron: Asymmetry 1995, 6, 263-269.
33. (a) Jefford, W. C; Sledeski, W. A; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 949-952.
34. (b) Jefford, W. C; Sledeski, W. A; Rossier, J-C.; Boukouvalas, J. Tetrahedron Lett. 1990, 31, 5741-5744.
35. For a review of stereoselective reaction of 2-(trimethylsilyloxy)furans and analogous dienes, see. Casiraghi, G.; Rassu, G. Synthesis 1995, 607-626.
36. A part of this study has been communicated: Kitajima, H.; Katsuki, T. Synlett 1997, 568-570.
37. 3-catalyzed reactions, see: Kobayashi, S. Synlett 1994, 689-701.
38. (a) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535-4538.
39. (b) Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325-6328.
40. (c) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083-4084.
41. (d) Kobayashi, S.; Ishitani, H.; Hachiya, I.; Araki, M. Tetrahedron 1994, 50, 11623-11636.
42. (e) Kobayashi, S.; Araki, M.; Hachiya, I. J. Org. Chem. 1994, 59, 3758-3759.
43. (a) Kitajima, H.; Aoki, Y.; Ito, K.; Katsuki, T., Chem. Lett. 1995, 1113-1114.
44. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn. 1997, 70, 207-217.
45. Kitajima, H.; Ito, K.; Katsuki, T. Chem. Lett. 1996, 343-344.
46. Advantageous effect of activated MS 4A on enantioselectivity has been reported for 1,3-dipolar cycloaddition reaction of nitrones catalyzed by Mg(II)-bis(oxazoline) complex: Gothelf, V. K.; Hazell, G. R.; Jørgensen, A. K. J. Org. Chem. 1996, 61, 346-355.
47. Taguchi et al. reported that enantioselectivity of the Michael reaction of α,β-unsaturated ketones using (S)-(2-pyrrolidyl)alkyl ammonium hydroxide as a chiral source was also remarkably improved by the addition of HFIP, the role of which was considered to accelerate the formation of the intermediary iminium salt and to reduce the basicity of the chiral source: Kawara, A.; Taguchi, T. Tetrahedron Lett. 1994, 35, 8805-8808.
48. For a review of the reactions using Cu(II)-bis(oxazoline) complexes as catalysts, see: Pfaltz, A. Acc. Chem. Res. 1993, 26, 339-345, and references cited therein.
49. For recent study using this type of complex, see also: (a) Evans, D. A.; Murry, A. J.; Kozlowski, C. M. J. Am. Chem. Soc. 1996, 118, 5814-5815.
50. (b) Sibi, P. M.; Ji, J. Wu, H. J.; Gürtler, S.; Porter, A. N. J. Am. Chem. Soc. 1996, 118, 9200-9201.
51. (a) Evans, D. A.; Miller, J. S.; Lectka, T. J. Am. Chem. Soc. 1993, 115, 6460-6461.
52. (b) Evans, D. A.; Kozlowski, C. M.; Tedrow, S. J. Tetrahedron Lett. 1996, 37, 7481-7484.
53. After we had completed our study, asymmetric Mukaiyama-Michael reaction using Cu(II)-bis(oxaxoline) complexes as catalyst was reported, though enantioselectivity was moderate (up to 66% ee): Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921-8924.
54. 2-5b complex was sluggish.
55. (a) Latypov, K. S.; Seco, M. J.; Quiñoá, E.; Riguera, R. J. Org. Chem. 1995, 60, 504-515.
56. (b) Kusumi, T.; Takahashi, H.; Xu, P.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inoue, Y. Tetrahedron Lett. 1994, 35, 4397-4410.
57. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717-1724.