Silicon as a controlling element for regioselective ene reaction of diethyl azodicarboxylate with (homo)allylic silanes. Applications to the synthesis of cyclic 1,2-dinitrogen compounds

Tetrahedron Letters

Volumn 37, Issue 36, 1996, Pages 6607-6610

  Sarkar, Tarun K ^a   Ghorai, Binay K ^a   Das, Shyamal K ^a   Gangopadhyay, Pulak ^a   Rao, P S V Subba ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZOLINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030565558     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01411-6     Document Type: Article

References (26)

1. Alder, K.; Pascher, F.; Schmitz, A. Ber. Dtsch. Chem. Ges. 1943, 76B, 27.
2. Gollnick, K.; Schenck, G.O. In "1,4-Cycloaddition Reactions. The Diels Alder Reaction in Heterocyclic Synthesis;" Hamer, J., Ed.; Academic Press : New York,New York, 1967, 8, pp. 255.
3. Houk, K.N.; Williams, J.C., Jr.; Mitchell, P.A.; Yamaguchi, K.J. J. Amer. Chem. Soc. 1981, 103, 949.
4. Clennan, E.L.; Chen, X.; Koola, J.J. J. Amer. Chem. Soc. 1990, 112, 5193.
5. Stephenson, L.M. Tetrahedron Lett. 1980, 21, 1005.
6. Clennan, E.L.; Koola, J.J.; Oolman, K.A. Tetrahedron Lett. 1990, 31, 6759.
7. Elemes, Y.; Stratakis, M.; Orfanopoulos, M. Tetrahedron Lett. 1989, 6903.
8. Orfanopoulos, M.; Stratakis, M.; Elemes, Y. Tetrahedron Lett. 1989, 30, 4875.
9. Orfanopoulos, M.; Stratakis, M.; Elmes, Y. J. Amer. Chem. Soc. 1990, 112, 6417.
10. Orfanopoulos, M.; Stratakis, M..; Elemes, Y.; Jensen, F. J. Amer. Chem. Soc. 1991, 113, 3180.
11. Mikami, K; Loh, T.P.; Nakai, T. J. Amer. Chem. Soc. 1990, 112, 6737.
12. Orfanopoulos, M.; Stratakis, M. Tetrahedron Lett. 1991, 32, 7321.
13. Clennan, E.L.; Koola, J.J. J. Amer. Chem. Soc. 1993, 115, 3802.
14. For a review see : Lambert, J.B. Tetrahedron. 1990, 46, 2677.
15. Dubac, J.; Laporterie, A.; Iloughmane, H.; Pillot, J.P.; Deleris, G.; Dunogues, J. J. Organomet. Chem. 1985, 281, 149.
16. For a review on ene and retro-ene reactions in group 14 organometallic chemistry : Dubac, J.; Laporterie, A. Chem. Rev. 1987, 87, 319.
17. Hoffmann, H.M.R. Angew. Chem. Int. Ed. Engl. 1969, 8, 556.
18. Thaler, W.A. Franzus, B. J. Org. Chem. 1964, 29, 2226.
19. Taber, D.F. "Intramolecular Diels-Alder and Alder Ene Reactions", Springer-Verlag, Berlin, 1984, pp. 66.
20. In a number of related pericyclic reactions, either accelerating or retarding influence of the IMS substituent has been documented : (a) Magnus, P.; Cairns, P.M.; Moursoundis, J. J. Amer. Chem. Soc. 1987, 109, 2469.
21. (b) Fleming, I.; Goldhill, J.; Perry, D.A. J. Chem. Soc. Perk 1, 1982, 1563.
22. Laporterie, A.; Dubac, J.; Lesbre, M. J. Organomet. Chem. 1975, 101, 187.
23. 1H-NMR and capillary GC.
24. (a) Rutjes, F.P.J.T.; Hiemstra, H.; Mooiweer, H.H.; Speckamp, W.N. Tetrahedron Lett. 1988, 29, 6975.
25. (b) Rutjes, F.P.J.T.; Teerhuis, M.; Hiemstra, H.; Speckamp, W.N. Tetrahedron 1993, 49, 8605.
26. 3) δ 157.35(s), 157.29(s), 141.69(s), 141.58(s), 136.49(d), 133.14(d), 128.46(d), 128.33(d), 128.14(d), 127.40(d), 125.87(d), 118.84(t), 117.06(t), 62.51(t), 62.39(t), 62.31(t), 62.24(t), 51.85(t), 50.38(t), 51.11(d), 47.07 (d), 35.91(t), 32.64(t), 32.36(t), 29.76(t), 14.54(q), 14.47(q).