Preparation of substituted indolines via anionic cyclization

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2596-2597

  Bailey, William F ^a   Jiang, Xing Long ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029902751     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960305p     Document Type: Article

References (34)

1. (a) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, Mechanisms of Importance in Synthesis, pp 251-273.
2. (b) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999.
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6. (f) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788.
7. (g) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765.
8. (h) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058.
9. (i) Krief, A.; Barbeaux, P. Synlett 1990, 511.
10. (j) Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417,
11. (k) Bailey, W. F.; Khanolkar, A. D. Tetrahedron Lett. 1990, 31, 5993.
12. (l) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K.; Ovaska, T. V.; Rossi, K.; Thiel, Y.; Wiberg, K. B. J. Am. Chem. Soc. 1901, 113, 5720.
13. (m) Bailey, W F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053.
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17. While the cyclization of 5-hexenyllithium and related species may be viewed as a formally anionic process, it should be noted that the lithium atom is intimately involved in the rearrangement. Indeed, 5-hexenyllithium is unique among the 5-hexenylalkalis in it ability to undergo facile cyclization. See: Bailey, W. F.; Punzalan, E. R. J. Am. Chem. Soc. 1994, 116, 6577.
18. To date, the only published investigations of heteroatom-containing 5-hexenyllithiums involve (2-oxa-5-hexenyl)-, (3-oxa-5-hexenyl)-, and (4-oxa-5-hexenyl)lithiums. For the 2-oxa system, which undergoes 5-exo closure on warming to give [(3-tetrahydrofuranyl)methyl]lithiums in good yield, see: (a) Broka, C. A.; Lee, W. J.; Shen, T. J. Org. Chem. 1988, 53, 1336. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (3-Oxa-5-hexenyl)lithium is inherently unstable and fragments at low temperature via β-elimination: Bailey, W. F.; Punzalan, E. R.; Zarcone, L. M. J. Heteroat. Chem. 1992, 3, 55. The 4-oxa system isomerizes on warming to give the lithium salt of a 4-alken-1-ol in the formal equivalent of a [1,4]-Wittig rearrangement: Bailey, W. F.; Zarcone, L. M. J. Tetrahedron Lett. 1991, 32, 4425.
19. To date, the only published investigations of heteroatom-containing 5-hexenyllithiums involve (2-oxa-5-hexenyl)-, (3-oxa-5-hexenyl)-, and (4-oxa-5-hexenyl)lithiums. For the 2-oxa system, which undergoes 5-exo closure on warming to give [(3-tetrahydrofuranyl)methyl]lithiums in good yield, see: (a) Broka, C. A.; Lee, W. J.; Shen, T. J. Org. Chem. 1988, 53, 1336. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (3-Oxa-5-hexenyl)lithium is inherently unstable and fragments at low temperature via β-elimination: Bailey, W. F.; Punzalan, E. R.; Zarcone, L. M. J. Heteroat. Chem. 1992, 3, 55. The 4-oxa system isomerizes on warming to give the lithium salt of a 4-alken-1-ol in the formal equivalent of a [1,4]-Wittig rearrangement: Bailey, W. F.; Zarcone, L. M. J. Tetrahedron Lett. 1991, 32, 4425.
20. To date, the only published investigations of heteroatom-containing 5-hexenyllithiums involve (2-oxa-5-hexenyl)-, (3-oxa-5-hexenyl)-, and (4-oxa-5-hexenyl)lithiums. For the 2-oxa system, which undergoes 5-exo closure on warming to give [(3-tetrahydrofuranyl)methyl]lithiums in good yield, see: (a) Broka, C. A.; Lee, W. J.; Shen, T. J. Org. Chem. 1988, 53, 1336. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (3-Oxa-5-hexenyl)lithium is inherently unstable and fragments at low temperature via β-elimination: Bailey, W. F.; Punzalan, E. R.; Zarcone, L. M. J. Heteroat. Chem. 1992, 3, 55. The 4-oxa system isomerizes on warming to give the lithium salt of a 4-alken-1-ol in the formal equivalent of a [1,4]-Wittig rearrangement: Bailey, W. F.; Zarcone, L. M. J. Tetrahedron Lett. 1991, 32, 4425.
21. To date, the only published investigations of heteroatom-containing 5-hexenyllithiums involve (2-oxa-5-hexenyl)-, (3-oxa-5-hexenyl)-, and (4-oxa-5-hexenyl)lithiums. For the 2-oxa system, which undergoes 5-exo closure on warming to give [(3-tetrahydrofuranyl)methyl]lithiums in good yield, see: (a) Broka, C. A.; Lee, W. J.; Shen, T. J. Org. Chem. 1988, 53, 1336. (b) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981. (3-Oxa-5-hexenyl)lithium is inherently unstable and fragments at low temperature via β-elimination: Bailey, W. F.; Punzalan, E. R.; Zarcone, L. M. J. Heteroat. Chem. 1992, 3, 55. The 4-oxa system isomerizes on warming to give the lithium salt of a 4-alken-1-ol in the formal equivalent of a [1,4]-Wittig rearrangement: Bailey, W. F.; Zarcone, L. M. J. Tetrahedron Lett. 1991, 32, 4425.
22. (a) Preobrazhenskaya, M. N. Russ. Chem. Rev. 1967, 36, 753.
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29. (g) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman and Hall: New York, 1995; pp 305-349
30. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
31. 13C NMR spectra are fully in accord with the assigned structures.
32. Lemaire-Audoire, S.; Savignac, M.; Genẽt, J. P.; Bernard, J.-M. Tetrahedron Lett. 1995, 36, 1267.
33. Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, xxxx.
34. Tidwell, J H.; Buchwald, S. L. J Am. Chem. Soc. 1994, 116, 11797 and references therein.