Syn-Selective Michael Addition of Nitromethane Derivatives to Enoates Derived from (R)-(+)-Glyceraldehyde Acetonide

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 4002-4006

  Costa, Jeronimo S ^a   Dias, Ayres G ^a,b   Anholeto, Aline L ^a   Monteiro, Mônica D ^a   Patrocinio, Vera L ^a   Costa, Paulo R R ^a  

^a Cd Univ Ilha do Governador   (Brazil)

^b STATE UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000209657     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960788x     Document Type: Article

References (42)

1. (a) Yamamoto, Y.; Pyne, S. G.; Schinzer, D.; Feringa, B. L.; Jansen J. F. G. A. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E 21b. Little, R. D.; Masjedizadeh, M. R. Org. React. 1995, 47, 315. Cook, C. E.; Allen, D. A.; Miller, D. B.; Whisnant, C. C. J. Am. Chem. Soc. 1995, 117, 7269. d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555.
2. (a) Yamamoto, Y.; Pyne, S. G.; Schinzer, D.; Feringa, B. L.; Jansen J. F. G. A. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E 21b. Little, R. D.; Masjedizadeh, M. R. Org. React. 1995, 47, 315. Cook, C. E.; Allen, D. A.; Miller, D. B.; Whisnant, C. C. J. Am. Chem. Soc. 1995, 117, 7269. d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555.
3. (a) Yamamoto, Y.; Pyne, S. G.; Schinzer, D.; Feringa, B. L.; Jansen J. F. G. A. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E 21b. Little, R. D.; Masjedizadeh, M. R. Org. React. 1995, 47, 315. Cook, C. E.; Allen, D. A.; Miller, D. B.; Whisnant, C. C. J. Am. Chem. Soc. 1995, 117, 7269. d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555.
4. (a) Yamamoto, Y.; Pyne, S. G.; Schinzer, D.; Feringa, B. L.; Jansen J. F. G. A. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E 21b. Little, R. D.; Masjedizadeh, M. R. Org. React. 1995, 47, 315. Cook, C. E.; Allen, D. A.; Miller, D. B.; Whisnant, C. C. J. Am. Chem. Soc. 1995, 117, 7269. d'Angelo, J.; Cavé, C.; Desmaele, D.; Dumas, F. Trends Org. Chem. 1993, 4, 555.
5. (b) Leonard, J. Contemp. Org. Synth. 1994, 387.
6. (c) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
7. Yoshida, S.; Yamanaka, J.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 7271. Revesz, L.; Briswalter, C.; Heng, R.; Leutwiler, A.; Mueller, R.; Wuethrich, H. Tetrahedron Lett. 1994, 35, 9693. Sniajda, W.; Zahouily, M.; Malacria, M. Tetrahedron Lett. 1992, 38, 5511.
8. Yoshida, S.; Yamanaka, J.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 7271. Revesz, L.; Briswalter, C.; Heng, R.; Leutwiler, A.; Mueller, R.; Wuethrich, H. Tetrahedron Lett. 1994, 35, 9693. Sniajda, W.; Zahouily, M.; Malacria, M. Tetrahedron Lett. 1992, 38, 5511.
9. Yoshida, S.; Yamanaka, J.; Miyake, T.; Moritani, Y.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1995, 36, 7271. Revesz, L.; Briswalter, C.; Heng, R.; Leutwiler, A.; Mueller, R.; Wuethrich, H. Tetrahedron Lett. 1994, 35, 9693. Sniajda, W.; Zahouily, M.; Malacria, M. Tetrahedron Lett. 1992, 38, 5511.
10. Leonard, J.; Mohialdin, S.; Swain, P. A. Synth. Commun. 1989, 19, 3529. Mann, J.; Partlett, N.; Thomaz, A. J. Chem. Res., Synop. 1987, 369, Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391.
11. Leonard, J.; Mohialdin, S.; Swain, P. A. Synth. Commun. 1989, 19, 3529. Mann, J.; Partlett, N.; Thomaz, A. J. Chem. Res., Synop. 1987, 369, Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391.
12. Leonard, J.; Mohialdin, S.; Swain, P. A. Synth. Commun. 1989, 19, 3529. Mann, J.; Partlett, N.; Thomaz, A. J. Chem. Res., Synop. 1987, 369, Marshall, J. A.; Trometer, J. D.; Cleary, D. G. Tetrahedron 1989, 45, 391.
13. Patrocinio, V. L.; Costa, P. R. R.; Correia, C. R. D. Synthesis 1994, 474.
14. Nomura, M.; Kanemasa, S. Tetrahedron Lett. 1994, 35, 143.
15. Nilsson, K.; Ullenius, C. Tetrahedron 1994, 50, 13173.
16. Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827. Morikawa, T.; Washio, Y; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1, 271.
17. Matsubara, S.; Yoshioka, M.; Utimoto, K. Chem. Lett. 1994, 827. Morikawa, T.; Washio, Y; Harada, S.; Hanai, R.; Kayashita, T.; Nemoto, H.; Shiro, M.; Taguchi, T. J. Chem. Soc., Perkin Trans. 1 1995, 1, 271.
18. For recent studies in racemic series on the Michael of nitronates see, inter alia: Francke, W.; Schröder, F.; Walter, F.; Sinnwell, V.; Baumann, H.; Kaib, M. Liebigs Ann. 1995, 965. Thomas, A.; Rajappa, S. Tetrahedron 1995, 51, 10571. Ballini, R.; Marziali, P.; Mozzicafreddo, A J. Org. Chem. 1996, 61, 3209. Marti, R. E.; Helnzer, J.; Seebach, D. Liebigs Ann. Chem. 1995, 7, 1193.
19. For recent studies in racemic series on the Michael of nitronates see, inter alia: Francke, W.; Schröder, F.; Walter, F.; Sinnwell, V.; Baumann, H.; Kaib, M. Liebigs Ann. 1995, 965. Thomas, A.; Rajappa, S. Tetrahedron 1995, 51, 10571. Ballini, R.; Marziali, P.; Mozzicafreddo, A J. Org. Chem. 1996, 61, 3209. Marti, R. E.; Helnzer, J.; Seebach, D. Liebigs Ann. Chem. 1995, 7, 1193.
20. For recent studies in racemic series on the Michael of nitronates see, inter alia: Francke, W.; Schröder, F.; Walter, F.; Sinnwell, V.; Baumann, H.; Kaib, M. Liebigs Ann. 1995, 965. Thomas, A.; Rajappa, S. Tetrahedron 1995, 51, 10571. Ballini, R.; Marziali, P.; Mozzicafreddo, A J. Org. Chem. 1996, 61, 3209. Marti, R. E.; Helnzer, J.; Seebach, D. Liebigs Ann. Chem. 1995, 7, 1193.
21. For recent studies in racemic series on the Michael of nitronates see, inter alia: Francke, W.; Schröder, F.; Walter, F.; Sinnwell, V.; Baumann, H.; Kaib, M. Liebigs Ann. 1995, 965. Thomas, A.; Rajappa, S. Tetrahedron 1995, 51, 10571. Ballini, R.; Marziali, P.; Mozzicafreddo, A J. Org. Chem. 1996, 61, 3209. Marti, R. E.; Helnzer, J.; Seebach, D. Liebigs Ann. Chem. 1995, 7, 1193.
22. (a) Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213. Ono, N.; Kamimura A.; Kaji, A. Synthesis 1984, 226.
23. (a) Ballini, R.; Bosica, G. Tetrahedron 1995, 51, 4213. Ono, N.; Kamimura A.; Kaji, A. Synthesis 1984, 226.
24. (b) Clark, J. H. Chem. Rev. 1980, 80, 429.
25. 2O in THF can lead to a decrease in the chemical yield.
26. Leonard, J.; Mohialdin, S.; Reed, D.; Ryan, G.; Jones, M. F. J. Chem. Soc., Chem. Commun. 1993, 23.
27. (a) Ziegler, F. E.; Tung, J. S. J. Org. Chem. 1991, 56, 6530 and references cited therein.
28. (b) Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365 and references cited therein.
29. Ono, N.; Miyake, H.; Kati, A. J. Org. Chem. 1984, 49, 4997.
30. Whener, V.; Jägger, V. Angew Chem., Int. Ed. Engl. 1990, 29, 1169. Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261.
31. Whener, V.; Jägger, V. Angew Chem., Int. Ed. Engl. 1990, 29, 1169. Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261.
32. Dorigo, A. E.; Morokuma, K. J. Am. Chem. Soc. 1989, 111, 6524.
33. (a) Bernardi, A.; Capelli, A. M.; Gennari, C.; Scolastico, C. Tetrahedron: Asymmetry 1990, 1, 21.
34. (b) Casas, R.; Parella, T.; Branchadell, V.; Oliva, A.; Ortuno, R. M. Tetrahedron 1992, 48, 2659.
35. 1H NMR that for E-enoates bearing an alkoxy group at the stereogenic center the main conformer has H-3 (at the olefinic β-carbon) and H-4 (at the stereogenic center) in an antiperiplanar relationship: Gung, B. W.; Melnick, J. P.; Wolf, M. A.; King, A. J. Org. Chem. 1995, 60, 1947 and references cited therein. The s-cis/s-trans conformational preferences of the ester group in enoates has been studied by supersonic jet spectroscopy, NOE, and X-ray analyses: Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
36. 1H NMR that for E-enoates bearing an alkoxy group at the stereogenic center the main conformer has H-3 (at the olefinic β-carbon) and H-4 (at the stereogenic center) in an antiperiplanar relationship: Gung, B. W.; Melnick, J. P.; Wolf, M. A.; King, A. J. Org. Chem. 1995, 60, 1947 and references cited therein. The s-cis/s-trans conformational preferences of the ester group in enoates has been studied by supersonic jet spectroscopy, NOE, and X-ray analyses: Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
37. 15b The calculation of transition states for the addition of nitronates to these conformers is under investigation. Amorim, M. B.; Filho, U. F.; Lima, P. G.; Costa, P. R. R. Unpublished results.
38. The anti-periplanar approximation has been proposed to explain the stereoselectivity in other Michael addition and aldol addition where a metal is not available for coordination. Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B. See also ref 1c.
39. Rosini, G.; Ballini, R. Synthesis 1988, 833. Seebach, D.; Colvin, E.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
40. Rosini, G.; Ballini, R. Synthesis 1988, 833. Seebach, D.; Colvin, E.; Lehr, F.; Weller, T. Chimia 1979, 33, 1.
41. Kornblum, N. Org. React. 1962, 12, 101.
42. Öhr, R.; Schwab,W; Ehrler, R.; Jäger, V. Synthesis 1986, 535.