Stereocontrolled Synthesis of 5-Acyl-3,4-dihydro-2H-pyrroles and Related Heterocycles via Intramolecular 2-Propylidene-1,3-bis(silane)-Acylnitrilium Ion Cyclizations

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 805-812

  Kercher, Timothy ^a   Livinghouse, Tom ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030936393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961452q     Document Type: Article

References (26)

1. Overman, L. E.; Ricca, D. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, Chapter 4.4 and references therein.
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9. Kercher, T.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 4200.
10. For a comprehensive account dealing with the synthetic utility of allylsilanes and related compounds see: The Electrophilic Substitution of Allylsilanes and Vinylsilanes. Fleming, I.: Dunogués. J.; Smithers, R. in Organic Reactions, Kende, A. S., Ed.; John Wiley and Sons: New York, 1989, Vol. 37, Chapter 2, p 57.
11. Several additional examples of stereocontrolled allylsilaneiminium ion cyclizations have appeared: (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Look, G. C.; Overman L. E. J. Org. Chem. 1993, 58, 6947. (b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (c) Hiemstra, H.; Forgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155. (d) Hiemstra. H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
12. Several additional examples of stereocontrolled allylsilaneiminium ion cyclizations have appeared: (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Look, G. C.; Overman L. E. J. Org. Chem. 1993, 58, 6947. (b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (c) Hiemstra, H.; Forgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155. (d) Hiemstra. H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
13. Several additional examples of stereocontrolled allylsilaneiminium ion cyclizations have appeared: (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Look, G. C.; Overman L. E. J. Org. Chem. 1993, 58, 6947. (b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (c) Hiemstra, H.; Forgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155. (d) Hiemstra. H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
14. Several additional examples of stereocontrolled allylsilaneiminium ion cyclizations have appeared: (a) Heerding, D. A.; Hong, C. Y.; Kado, N.; Look, G. C.; Overman L. E. J. Org. Chem. 1993, 58, 6947. (b) Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 11028. (c) Hiemstra, H.; Forgens, H. P.; Speckamp, W. N. Tetrahedron Lett. 1985, 26, 3155. (d) Hiemstra. H.; Sno, M. H. A. M.; Vijn, R. J.; Speckamp, W. N. J. Org. Chem. 1985, 50, 4014.
15. (a) Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am Chem Soc. 1986, 108, 3512.
16. (b) Grieco, P. A.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 5067.
17. In contrast to allylsilanes, 2-propylidene-1,3-bis(silane)s have seen relatively little use in synthesis. For pertinent references concerning the use of these compounds as well as related methodology, see: (a) Rubiralt, M.; Diez, A.; Miguel, D. Syn. Commun. 1992, 22, 359. (b) Guyot, B.; Pornet, J.; Miginiac, L. J. Organomet. Chem. 1990, 386, 19. (c) Guyot, B.; Pornet, J.; Miginiac, L. Tetrahedron 1991, 47, 3981.
18. In contrast to allylsilanes, 2-propylidene-1,3-bis(silane)s have seen relatively little use in synthesis. For pertinent references concerning the use of these compounds as well as related methodology, see: (a) Rubiralt, M.; Diez, A.; Miguel, D. Syn. Commun. 1992, 22, 359. (b) Guyot, B.; Pornet, J.; Miginiac, L. J. Organomet. Chem. 1990, 386, 19. (c) Guyot, B.; Pornet, J.; Miginiac, L. Tetrahedron 1991, 47, 3981.
19. In contrast to allylsilanes, 2-propylidene-1,3-bis(silane)s have seen relatively little use in synthesis. For pertinent references concerning the use of these compounds as well as related methodology, see: (a) Rubiralt, M.; Diez, A.; Miguel, D. Syn. Commun. 1992, 22, 359. (b) Guyot, B.; Pornet, J.; Miginiac, L. J. Organomet. Chem. 1990, 386, 19. (c) Guyot, B.; Pornet, J.; Miginiac, L. Tetrahedron 1991, 47, 3981.
20. An account addressing stereoselective cyclizations of allylsilanes with nitrilium ions generated by a Beckmann rearrangement has appeared, see: Schinzer, D.; Bo, Y. Angew. Chem., Int. Ed. Engl. 1991, 30, 687.
21. Danishefsky, S.; McKee, R.; Singh, R. K. J. Am. Chem. Soc. 1977, 99, 771.
22. 13C NMR, IR and possess satisfactory combustion analyses or exact mass.
23. Krimen, L. I. in Organic Syntheses; Breslow, R., Ed.; John Wiley and Sons: New York, 1970; Vol. 50, p 1.
24. For a recent review see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
25. In contrast to the cis-pyrrolines, the only significant NOE enhancements which were observed upon irradiation of the C-4 and C-2 methine hydrogens in the minor trans isomers were to different hydrogens on the central C-3 methylene: Chemical equations presented
26. In related pyrrolidine systems, Overman has observed epimerization upon exposure to silica gel during chromatography: Deng, W.; Overman, L. E. J. Am. Chem. Soc 1994, 116, 11241.