Syn-SN2′ Pathway in the Reaction of Certain γ-(Mesyloxy) α,β-Enoates with RCu(CN)MgX·BF3 Reagents. Importance of MgX and Bulky R Group upon the Diastereoselectivity

Journal of Organic Chemistry

Volumn 58, Issue 5, 1993, Pages 1207-1214

  Ibuka, Toshiro ^a   Taga, Tooru ^a   Habashita, Hiromu ^a   Nakai, Kazuo ^a   Tamamura, Hirokazu ^a   Fujii, Nobutaka ^a   Chounan, Yukiyasu ^b   Nemoto, Hisao ^b   Yamamoto, Yoshinori ^b  

^a KYOTO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001388469     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00057a038     Document Type: Article

References (79)

1. Magid, R. M. Tetrahedron 1980, 36, 1901.
2. Marshall, J. A. Chem. Rev. 1989, 89, 1503.
3. Lipshutz, B. H. Synlett 1990, 119.
4. Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
5. Trost, B. M.; Klun, T. P. J. Org. Chem. 1980, 45, 4257.
6. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1983, 48, 721.
7. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1984, 49, 422.
8. Goering, H. L.; Kanter, S. S.; Seitz, E. P., Jr. J. Org. Chem. 1985, 50, 5495.
9. Tseng, C. C.; Yen, S.-J.; Goering, H. L. J. Org. Chem. 1986, 51, 2892.
10. Tseng, C. C.; Paisley, S. D.; Goering, H. L. J. Org. Chem. 1986, 51, 2884.
11. Curran, D. P.; Chen, M.-H.; Leszezweski, D.; Elliott, R. L.; Rakiewicz, D. M. J. Org. Chem. 1986, 51, 1612.
12. Underiner, T. L.; Goering, H. L. J. Org. Chem. 1988, 53, 1140.
13. Ibuka, T.; Nakao, T.; Nishii, S.; Yamamoto, Y. J. Am. Chem. Soc. 1986, 108, 7420.
14. Ibuka, T.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1987, 1596.
15. Ibuka, T.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Am. Chem. Soc. 1989, 111, 4864.
16. Ibuka, T.; Akimoto, N.; Tanaka, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1989, 54, 4055.
17. Ibuka, T.; Tanaka, M.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1989, 967.
18. Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. Angew. Chem., Int. Ed. Engl. 1990, 29, 801.
19. Ibuka, T.; Habashita, H.; Otaka, A.; Fujii, N.; Oguchi, Y.; Uyehara, T.; Yamamoto, Y. J. Org. Chem. 1991, 56, 4370.
20. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834.
21. Kempf, D. J.; Wang, X. C.; Spanton, S. G. Int. J. Pept. Protein Res. 1991, 38, 237.
22. Yamamoto, Y.; Tanaka, M.; Ibuka, T. J. Org. Chem. 1992, 57, 1024.
23. Marino, J. P.; Kelly, M. G. J. Org. Chem. 1981, 46, 4389.
24. Marino, J. P.; Jaén, J. C. J. Am. Chem. Soc. 1982, 104, 3165.
25. Marino, J. P.; Fernández de la Pradilla, R.; Laborde, E. J. Org. Chem. 1987, 52, 4898.
26. Marshall, J. A.; Trometer, J. D. Tetrahedron Lett. 1987, 28, 4985.
27. Marshall, J. A.; Trometer, J. D.; Blough, B. E.; Crute, T. D. Tetrahedron Lett. 1988, 29, 913.
28. Marshall, J. A.; Trometer, J. D.; Cleary, D. J. Tetrahedron 1989, 45, 391.
29. Marshall, J. A.; Blough, B. E. J. Org. Chem. 1990, 55, 1540.
30. Marshall, J. A.; Blough, B. E. J. Org. Chem. 1991, 56, 2225.
31. Marshall, J. A.; Crute, T. D., III; Hsi, J. D. J. Org. Chem. 1992, 57, 115.
32. Tanigawa, Y.; Kanamaru, H.; Murahashi, S.-I. J. Am. Chem. Soc. 1977, 99, 2361.
33. Tanigawa, Y.; Ohta, H.; Sonoda, A.; Murahashi, S.-I. J. Am. Chem. Soc. 1978, 100, 4610.
34. Goering, H. L.; Kantner, S. S. J. Org. Chem. 1981, 46, 2144.
35. Yanagisawa, A.; Noritake, Y.; Nomura, N.; Yamamoto, H. Synlett 1991, 251.
36. See also: Yanagisawa, A.; Nomura, N.; Yamamoto, H. Synlett. 1991, 513.
37. Yanagisawa, A.; Nomura, N.; Noritake, Y.; Yamamoto, H. Synthesis 1991, 1130.
38. Nakamura, E.; Sekiya, K.; Arai, M.; Aoki, S. J. Am. Chem. Soc. 1989, 111, 3091.
39. Arai, M.; Nakamura, E.; Lipshutz, B. H. J. Org. Chem. 1991, 56, 5489.
40. Gallina, C.; Ciattini, P. G. J. Am. Chem. Soc. 1979, 101, 1035.
41. Gallina, C. Tetrahedron Lett. 1982, 23, 3093.
42. Goering, H. L.; Kantner, S. S.; Tseng, C. C. J. Org. Chem. 1983, 48, 715.
43. Fleming, I.; Thomas, A. P. J. Chem. Soc., Chem. Commun. 1986, 1456.
44. RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, P. J. J. Am. Chem. Soc. 1988, 110, 7128.
45. Greene, A. E.; Coelho, F.; Depres, J.-P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661.
46. Underiner, T. L.; Goering, H. L. J. Org. Chem. 1989, 54, 3239.
47. Denmark, S. E.; Marble, L. K. J. Org. Chem. 1990, 55, 1984.
48. Hutchinson, D. K.; Fuchs, P. L. J. Am. Chem. Soc. 1985, 107, 6137.
49. Hutchinson, D. K.; Hardinger, S. A.; Fuchs, P. L. Tetrahedron Lett. 1986, 27, 1425.
50. Hutchinson, D. K.; Fuchs, P. L. Tetrahedron Lett. 1986, 27, 1429.
51. Pan, V.; Hutchinson, D. K.; Nantz, M. H.; Fuchs, P. L. Tetrahedron 1989, 45, 467.
52. Berglund, R. A.; Braish, T. F.; Jakubowski, J. A.; Fuchs, P. L. Bioorg. Med. Chem. 1991, 1, 649.
53. Marshall, J. A.; Audia, V. H.; Jenson, T. M.; Guida, W. C. Tetrahedron 1986, 42, 1703.
54. Marshall, J. A.; Audia, V. H. J. Org. Chem. 1987, 52, 1106.
55. Ziegler, F. E.; Cady, M. A. J. Org. Chem. 1981, 46, 122.
56. Valverde, S.; Bernabé, M.; Garcia-Ochoa, S.;Gómez, A. M. J. Org. Chem. 1990, 55, 2294.
57. Miles, N. J.; Sammes, P. G.; Kennewell, P. D.; Westwood, R. J. Chem. Soc., Perkin Trans. 1 1985, 2299.
58. For a recent report, see: Coleman, R. S.; Carpenter, A. J. Tetrahedron Lett. 1992, 33, 1697 and references cited therein.
59. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrine, P. J. Org. Chem. 1990, 55, 1439.
60. Sham, H. L.; Rempel, C. A.; Stein, H.; Cohen, J. J. Chem. Soc., Chem. Commun. 1990, 904.
61. Patel, D. V.; R.-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587.
62. Friesen, R. W.; Kolaczewska, A. E. J. Org. Chem. 1991, 56, 4888.
63. Ibuka, T.; Habashita, H.; Funakoshi, S.; Fujii, N.; Baba, K.; Kozawa, M.; Oguchi, V.; Uyehara, T.; Yamamoto, Y. Tetrahedron: Asymmetry 1990, 1, 389.
64. See also: Ibuka, T.;Taga, T.;Shingu, T.;Saito, M.; Nishii, S.; Yamamoto, Y. J. Org. Chem. 1988, 53, 3947.
65. Johnson, F.; Malhotra, S. K. J. Am. Chem. Soc. 1965, 87, 5492.
66. See also: Paddon-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162.
67. Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 666.
68. Chamberlin, A. R.; Mulholland, R. L.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672.
69. Seebach, D.; Lamatsch, B.; Amstutz, R.; Beck, A. K.; Dobler, M.; Egli, M.; Fitzi, R.; Gautschi, M.; Herradón, B.; Hidber, F. C.; Irwin, J. J.; Locher, R.; Maestro, M.; Maetzke, T.; Mouriño, A.; Pfammatter, E.; Plattner, D. A.; Schickli, C.; Schweizer, W. B.; Seiler, P.; Stuckey, G.; Petter, W.; Escalante, J.; Juaristi, E.; Quintana, D.; Miravitlles, C.; Molins, E. Helv. Chim. Acta 1892, 75, 913.
70. As shown in Figure 5, for the stereochemistry of the tert-butoxycarbonyl group, two stereoisomers (A and B) can be drawn. The carbon atoms (C-2, C-4, and C-1′), the nitrogen atom, and the oxygen atoms (O-2′ and O-3′) would lie nearly on the same plane, (see: Hondrelis, J.; Lonergan, G.; Voliotis, S.; Matsoukas, J. Tetrahedron 1990, 46, 565.
71. See also: Shustov, G. V.; Kadorkina, G. K.; Varlamov, S. V.; Kachanov, A. V.; Kostyanovsky, R. G.; Rauk, A. J. Am. Chem. Soc. 1992, 114, 1616). Conformer B would be destabilized in comparison with A owing to unfavorable interactions between the bulky tert-butyl group and the gem-dimethyl group at the C-2 position. The NOESY spectrum and the selective decoupling experiment of 4 clearly indicated a NOE between the protons of the tert-butyl group and the proton on C-4 in Figure 5A. Furthermore, the crystal structure of 23 (Figure 1) shows that the stereochemistry of the Boc group in 23 is essentially the same as shown in structure A. (Figure presented.)
72. Ibuka, T.; Chu, G.-N.; Yoneda, F. Tetrahedron Lett. 1984, 25, 3247.
73. Ibuka, T.; Aoyagi, T.; Yoneda, F. J. Chem. Soc., Chem. Commun. 1985, 1452.
74. Takano, S.; Sekiguchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 449.
75. Fujii, N.; Habashita, H.; Shigemori, N.; Otaka, A.; Ibuka, T.; Tanaka, M.; Yamamoto, Y. Tetrahedron Lett. 1991, 32, 4969.
76. Ruden, R. A.;Litterer, W.E. Tetrahedron Lett. 1975, 2043.
77. Wege, P. M.; Clark, R. D.; Heathcock, C. H. J. Org. Chem. 1976, 41, 3144.
78. Logusch, E. W. Tetrahedron Lett. 1979, 3365.
79. Jackson, R. F. W.; Standen, S. P.; Clegg, W.; McCamley, A. Tetrahedron Lett. 1992, 33, 6197.