Addition of transiently-generated methyl o-lithiobenzoate to imines. An isoindolone annulation

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6205-6211

  Campbell, James B ^a   Dedinas, Robert F ^a   Trumbower Walsh, Sally A ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000525743     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960582w     Document Type: Article

References (39)

1. For recent examples of addition of organometallics to imines see: (a) Katritzky, A. R.; Hong, Q.; Yang, Z. J. Org. Chem. 1995, 60, 3405. (b) Higashiyama, K.; Fujikura, H.; Takahashi, H. Chem. Pharm Bull Tokyo 1995, 43, 722.
2. For recent examples of addition of organometallics to imines see: (a) Katritzky, A. R.; Hong, Q.; Yang, Z. J. Org. Chem. 1995, 60, 3405. (b) Higashiyama, K.; Fujikura, H.; Takahashi, H. Chem. Pharm Bull Tokyo 1995, 43, 722.
3. (a) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Am. Chem. Soc. 1984, 106, 5031.
4. (b) Wada, M.; Sakurai, Y.; Akiba, K. Tetrahedron Lett. 1984, 25, 1079.
5. (c) Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865.
6. Bradsher, C. K.; Hunt, D. A. J. Org. Chem. 1981, 46, 327.
7. Parham, W. E.; Jones, L. D. J. Org. Chem. 1976, 41, 2704.
8. Parham, W. E.; Jones, L. D. J. Org. Chem. 1976, 41, 1187.
9. Clark, R. D.; Jahangir J. Org. Chem. 1987, 52, 5378.
10. Puterbaugh, W. H.; Hauser, C. R. J. Org. Chem. 1964, 29, 853.
11. (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.12.
12. 2 promotes the addition of perfluoroalkylcarbanions to imines with acidic α-hydrogens. See: Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. For a discussion of the kinetic acidity of imine α-hydrogens see: Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 2166.
13. 2 promotes the addition of perfluoroalkylcarbanions to imines with acidic α-hydrogens. See: Uno, H.; Shiraishi, Y.; Shimokawa, K.; Suzuki, H. Chem. Lett. 1988, 729. For a discussion of the kinetic acidity of imine α-hydrogens see: Romesberg, F. E.; Collum, D. B. J. Am. Chem. Soc. 1995, 117, 2166.
14. Parham, W. E.; Sayed, Y. A. J. Org. Chem. 1974, 39, 2053.
15. Perfluoroalkyl carbanions: Reference 8. (a) Johncock, P. J. Organomet. Chem. 1969, 19, 257. (b) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243. Allyllithiums: (c) Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326. Alkenyllithiums: (c) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5209.
16. Perfluoroalkyl carbanions: Reference 8. (a) Johncock, P. J. Organomet. Chem. 1969, 19, 257. (b) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243. Allyllithiums: (c) Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326. Alkenyllithiums: (c) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5209.
17. Perfluoroalkyl carbanions: Reference 8. (a) Johncock, P. J. Organomet. Chem. 1969, 19, 257. (b) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243. Allyllithiums: (c) Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326. Alkenyllithiums: (c) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5209.
18. Perfluoroalkyl carbanions: Reference 8. (a) Johncock, P. J. Organomet. Chem. 1969, 19, 257. (b) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243. Allyllithiums: (c) Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326. Alkenyllithiums: (c) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5209.
19. Perfluoroalkyl carbanions: Reference 8. (a) Johncock, P. J. Organomet. Chem. 1969, 19, 257. (b) Gassman, P. G.; O'Reilly, N. J. Tetrahedron Lett. 1985, 26, 5243. Allyllithiums: (c) Katzenellenbogen, J. A.; Lenox, R. S. J. Org. Chem. 1973, 38, 326. Alkenyllithiums: (c) Flann, C. J.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6115. Lee, S. W.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5209.
20. (a) Rogers, H. R.; Houk, J. J. Am. Chem. Soc. 1982, 104, 522.
21. (b) Reich, H. J.; Phillips, N. H.; Reich, I. L. J. Am. Chem. Soc. 1985, 107, 4101.
22. (c) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
23. (d) Beak, p.; Musick, T. J.; Liu, C.; Cooper, T.; Gallagher, D. J. J. Org. Chem. 1993, 58, 7330.
24. 2, gave only ca. 20% of isoindolone 9d. Previous attempts to prepare organolithium reagents from stannanes in the presence of esters failed unless additional stabilizing groups were present. See: (a) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438. (b) Imanieh, H.; MacLeod, D.; Quayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 405. (c) Booth, C.; Imanieh, H.; Quayle, P.; Shui-Yu, L. Tetrahedron Lett. 1992, 33, 413.
25. 2, gave only ca. 20% of isoindolone 9d. Previous attempts to prepare organolithium reagents from stannanes in the presence of esters failed unless additional stabilizing groups were present. See: (a) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438. (b) Imanieh, H.; MacLeod, D.; Quayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 405. (c) Booth, C.; Imanieh, H.; Quayle, P.; Shui-Yu, L. Tetrahedron Lett. 1992, 33, 413.
26. 2, gave only ca. 20% of isoindolone 9d. Previous attempts to prepare organolithium reagents from stannanes in the presence of esters failed unless additional stabilizing groups were present. See: (a) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438. (b) Imanieh, H.; MacLeod, D.; Quayle, P.; Zhao, Y.; Davies, G. M. Tetrahedron Lett. 1992, 33, 405. (c) Booth, C.; Imanieh, H.; Quayle, P.; Shui-Yu, L. Tetrahedron Lett. 1992, 33, 413.
27. We also tried to exploit the dianion derived from o-bromobenzoic acid, especially given the reported stability of the dianion at -78°C. Isoindolones could be prepared in 35-45% yield. However, the poor solubility of the dianion tended to give variable results. See: Parham, W. E.; Sayed, Y. A. J. Org. Chem. 1974, 39, 2051.
28. Several other organolithium reagents were evaluated in the isoindolone annulation process. Both MeLi·LiBr and tert-butyllithium proved to be inferior to phenyllithium. nBuLi, when used in a strict stoichiometry of 1.30 equiv relative to the imine, gave good yields of isoindolone. However, small variations in the amount of nBuLi, e.g., 1.2 equiv, gave significantly lower yields.
29. Thies, H.; Schönenberger, H. Chem. Ber. 1956, 89, 1918.
30. Hale, J. J.; Finke, P. E.; MacCoss, M. Biorg.Med. Chem. Lett. 1993, 3, 319.
31. Stetin, C.; de Jeso, B.; Pommier, J. C. Synth. Commun. 1982, 12, 495.
32. We have chosen to formally designate the reactive species generated by the PhLi-induced lithium-iodide exchange on methyl o-iodobenzoate as theo-lithiated benzoate derivative. However, we have no structural evidence that confirms the lithio-derivative as the reactive intermediate. An alternative reactive intermediate might be a hypervalent "ate" complex. See: Reich, H. J.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1989, 111, 3444.
33. We have also added phenyllithium to a mixture of isopropyl o-iodobenzoate and trimethylsilyl chloride, at -78°C, to produce isopropyl o-(trimethylsilyl)benzoate in a 72% yield.
34. (a) Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1972; Vol. II, Chapter 12.
35. (b) Anderson, W. K.; Milowsky, A. S. J. Med. Chem. 1986, 29, 2241.
36. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879.
37. Watson, S. C.; Eastham, J. F. J. Organomet. Chem. 1967, 9, 165.
38. Bergbreiter, D. E.; Pendergrass, E. J. Org. Chem. 1981, 46, 219.
39. Brown, H. C.; Kramer, G. W.; Levy, A. B.; Midland, M. M. In Organic Synthesis via Boranes; John Wiley & Sons, Inc.: New York, 1975; Chapter 9.