Synthetic applications of the β-lithiation of β-Aryl secondary amides: Diastereoselective and enantioselective substitutions

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4542-4554

  Lutz, Gary P ^a   Du, Hua ^a   Gallagher, Donald J ^a   Beak, Peter ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001318144     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952223r     Document Type: Article

References (46)

1. For leading references and reviews on homoenolates, see: Kuwajima, I.; Nakamura, E. Topics Curr. Chem. 1991, 155, 1. Stowell, J. C. Chem. Rev. 1984, 84, 409.
2. For leading references and reviews on homoenolates, see: Kuwajima, I.; Nakamura, E. Topics Curr. Chem. 1991, 155, 1. Stowell, J. C. Chem. Rev. 1984, 84, 409.
3. Lutz, G. P.; Wallin, A. P.; Kerrick, S. T.; Beak, P. J. Org. Chem. 1991, 56, 4938. Beak, P.; Hunter, J. E.; Jun, Y. M.; Wallin, A. P. J. Am. Chem. Soc. 1987, 109, 5403. Beak, P.; Hunter, J. E.; Jun, Y. M. J. Am. Chem. Soc. 1983, 105, 6350.
4. Lutz, G. P.; Wallin, A. P.; Kerrick, S. T.; Beak, P. J. Org. Chem. 1991, 56, 4938. Beak, P.; Hunter, J. E.; Jun, Y. M.; Wallin, A. P. J. Am. Chem. Soc. 1987, 109, 5403. Beak, P.; Hunter, J. E.; Jun, Y. M. J. Am. Chem. Soc. 1983, 105, 6350.
5. Lutz, G. P.; Wallin, A. P.; Kerrick, S. T.; Beak, P. J. Org. Chem. 1991, 56, 4938. Beak, P.; Hunter, J. E.; Jun, Y. M.; Wallin, A. P. J. Am. Chem. Soc. 1987, 109, 5403. Beak, P.; Hunter, J. E.; Jun, Y. M. J. Am. Chem. Soc. 1983, 105, 6350.
6. Kinetic deprotonation of a less thermodynamically acidic hydrogen has been rationalized in terms of a complex-induced proximity effect (CIPE). Beak, P.; Meyers, A. I. Acc. Chem. Res. 1986, 19, 356.
7. For a preliminary report of this work, see: Beak, P.; Du, H. J. Am. Chem. Soc. 1993, 115, 2516.
8. Hunter, J. E. Ph.D. Dissertation, University of Illinois at Urbana-Champaign, 1986.
9. For related work, see: Hoppe, D.; Kramer, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 69. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2158 and references cited therein.
10. For related work, see: Hoppe, D.; Kramer, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 69. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2158 and references cited therein.
11. For related work, see: Hoppe, D.; Kramer, T. Angew. Chem., Int. Ed. Engl. 1989, 28, 69. Thayumanavan, S.; Lee, S.; Liu, C.; Beak, P. J. Am. Chem. Soc. 1994, 116, 9755. Hoppe, I.; Marsch, M.; Harms, K.; Boche, G.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 2158 and references cited therein.
12. 8 Work is currently underway exploring the mechanistic issues of these asymmetric substitution reactions, and the results will be presented in due course.
13. Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 102, 1257. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
14. Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 102, 1257. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
15. Hoppe, D.; Hintze, F.; Tebben, P. Angew. Chem., Int. Ed. Engl. 1990, 102, 1257. Kerrick, S. T.; Beak, P. J. Am. Chem. Soc. 1991, 113, 9708. Beak, P.; Kerrick, S. T.; Wu, S.; Chu, J. J. Am. Chem. Soc. 1994, 116, 3231.
16. 10
17. For recent applications of this reaction, see: Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. Pearson, A. J.; O'Brien, M. K. J. Org. Chem. 1989, 54, 4663-4673. Overman, L. E.; Wild, H. Tetrahedron Lett. 1989, 30, 647-650.
18. For recent applications of this reaction, see: Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. Pearson, A. J.; O'Brien, M. K. J. Org. Chem. 1989, 54, 4663-4673. Overman, L. E.; Wild, H. Tetrahedron Lett. 1989, 30, 647-650.
19. For recent applications of this reaction, see: Chan, T. H.; Pellon, P. J. Am. Chem. Soc. 1989, 111, 8737-8738. Pearson, A. J.; O'Brien, M. K. J. Org. Chem. 1989, 54, 4663-4673. Overman, L. E.; Wild, H. Tetrahedron Lett. 1989, 30, 647-650.
20. Oppolzer, W.; Mills, R. J.; Pachinger, W.; Stevenson, T. Helv. Chim. Acta 1986, 69, 1542-1545.
21. Touet, J.; Baudouin, S.; Brown, E. Tetrahedron: Asymmetry 1992, 3, 587-590.
22. Soai, K.; Ookawa, A. J. Chem. Soc., Perkin Trans. 1 1986, 759. Soai, K.; Ookawa, A.; Nohara, Y. Synth. Commun. 1983, 13, 27-334.
23. Soai, K.; Ookawa, A. J. Chem. Soc., Perkin Trans. 1 1986, 759. Soai, K.; Ookawa, A.; Nohara, Y. Synth. Commun. 1983, 13, 27-334.
24. Mukaiyaraa, T.; Iwasawa, N. Chem. Lett. 1981, 913-916.
25. Fang, C.; Ogawa, T.; Suemune, H.; Sakai, K. Tetrahedron: Asymetry 1991, 2, 389-398.
26. Meyers, A. I.; Smith, R. K.; Whitten, C. E. J. Org. Chem. 1979, 44, 2250-2254. Meyers, A. I.; Whitten, C. E. J. Am. Chem. Soc. 1975, 97, 6266-6267.
27. Meyers, A. I.; Smith, R. K.; Whitten, C. E. J. Org. Chem. 1979, 44, 2250-2254. Meyers, A. I.; Whitten, C. E. J. Am. Chem. Soc. 1975, 97, 6266-6267.
28. Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424-2426.
29. For recent reports on highly diastereoselective iodolactonization see: Hoffmann, R. W.; Stürmer, R.; Harms, K. Tetrahedron Lett. 1994, 35, 6263-6266. Friesen, R. W.; Kolaczewska, A. E. J. Org. Chem. 1991, 56, 4888-4895. Pearson, A. J.; Hsu, S-Y. J. Org. Chem. 1986, 51, 2505-2511. Metz, P. Tetrahedron 1993, 49, 6367-6374.
30. For recent reports on highly diastereoselective iodolactonization see: Hoffmann, R. W.; Stürmer, R.; Harms, K. Tetrahedron Lett. 1994, 35, 6263-6266. Friesen, R. W.; Kolaczewska, A. E. J. Org. Chem. 1991, 56, 4888-4895. Pearson, A. J.; Hsu, S-Y. J. Org. Chem. 1986, 51, 2505-2511. Metz, P. Tetrahedron 1993, 49, 6367-6374.
31. For recent reports on highly diastereoselective iodolactonization see: Hoffmann, R. W.; Stürmer, R.; Harms, K. Tetrahedron Lett. 1994, 35, 6263-6266. Friesen, R. W.; Kolaczewska, A. E. J. Org. Chem. 1991, 56, 4888-4895. Pearson, A. J.; Hsu, S-Y. J. Org. Chem. 1986, 51, 2505-2511. Metz, P. Tetrahedron 1993, 49, 6367-6374.
32. For recent reports on highly diastereoselective iodolactonization see: Hoffmann, R. W.; Stürmer, R.; Harms, K. Tetrahedron Lett. 1994, 35, 6263-6266. Friesen, R. W.; Kolaczewska, A. E. J. Org. Chem. 1991, 56, 4888-4895. Pearson, A. J.; Hsu, S-Y. J. Org. Chem. 1986, 51, 2505-2511. Metz, P. Tetrahedron 1993, 49, 6367-6374.
33. 1H NMR NOE experiment detailed in the Experimental Section.
34. Previous asymmetric syntheses of 4-substituted hydrocoumarins: Grimshaw, J.; Millar, P. G. J. Chem. Soc. 1970, 2324. Abe, S.; Nonaka, T.; Fuchigami, T. J. Am. Chem. Soc. 1983, 105, 3630-3632. Schoo, N.; Schafer, H.-J. Liebig. Ann. Chem. 1993, 601-607. Syntheses of racemic 4-substituted hydrocoumarins: Bergdahl, M.; Eriksson, M.; Nisson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. Patra, A.; Misra, S. K. Indian J. Chem. 1988, 272-273.
35. Previous asymmetric syntheses of 4-substituted hydrocoumarins: Grimshaw, J.; Millar, P. G. J. Chem. Soc. 1970, 2324. Abe, S.; Nonaka, T.; Fuchigami, T. J. Am. Chem. Soc. 1983, 105, 3630-3632. Schoo, N.; Schafer, H.-J. Liebig. Ann. Chem. 1993, 601-607. Syntheses of racemic 4-substituted hydrocoumarins: Bergdahl, M.; Eriksson, M.; Nisson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. Patra, A.; Misra, S. K. Indian J. Chem. 1988, 272-273.
36. Previous asymmetric syntheses of 4-substituted hydrocoumarins: Grimshaw, J.; Millar, P. G. J. Chem. Soc. 1970, 2324. Abe, S.; Nonaka, T.; Fuchigami, T. J. Am. Chem. Soc. 1983, 105, 3630-3632. Schoo, N.; Schafer, H.-J. Liebig. Ann. Chem. 1993, 601-607. Syntheses of racemic 4-substituted hydrocoumarins: Bergdahl, M.; Eriksson, M.; Nisson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. Patra, A.; Misra, S. K. Indian J. Chem. 1988, 272-273.
37. Previous asymmetric syntheses of 4-substituted hydrocoumarins: Grimshaw, J.; Millar, P. G. J. Chem. Soc. 1970, 2324. Abe, S.; Nonaka, T.; Fuchigami, T. J. Am. Chem. Soc. 1983, 105, 3630-3632. Schoo, N.; Schafer, H.-J. Liebig. Ann. Chem. 1993, 601-607. Syntheses of racemic 4-substituted hydrocoumarins: Bergdahl, M.; Eriksson, M.; Nisson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. Patra, A.; Misra, S. K. Indian J. Chem. 1988, 272-273.
38. Previous asymmetric syntheses of 4-substituted hydrocoumarins: Grimshaw, J.; Millar, P. G. J. Chem. Soc. 1970, 2324. Abe, S.; Nonaka, T.; Fuchigami, T. J. Am. Chem. Soc. 1983, 105, 3630-3632. Schoo, N.; Schafer, H.-J. Liebig. Ann. Chem. 1993, 601-607. Syntheses of racemic 4-substituted hydrocoumarins: Bergdahl, M.; Eriksson, M.; Nisson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238-7244. Patra, A.; Misra, S. K. Indian J. Chem. 1988, 272-273.
39. 20 The absolute configurations of 61, 63-66, 68, and 69 are assigned by analogy to (R)-67.
40. Suffert, J. J. Org. Chem. 1989, 54, 509.
41. 13C NMR spectra of 9 were consistent with previously reported data. De Kimpe, N.; Sulmon, P.; Moens, L.; Schamp, N.; Declercq, J.-P.; Meerssche, M. V. J. Org. Chem. 1986, 51, 3839.
42. 1H NMR spectrum, and mass spectrum of 31 were consistent with previously reported data. Campaigne, E.; Ellis, R. L. J. Org. Chem. 1967, 32, 2372. Baumann, N.; Sung, M.; Ulman, E. F. J. Am. Chem. Soc. 1968, 90, 4157.
43. 1H NMR spectrum, and mass spectrum of 31 were consistent with previously reported data. Campaigne, E.; Ellis, R. L. J. Org. Chem. 1967, 32, 2372. Baumann, N.; Sung, M.; Ulman, E. F. J. Am. Chem. Soc. 1968, 90, 4157.
44. Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1981, 913-916.
45. Pirkle, W. H.; McCune, J. F. J. Chromatogr. 1989, 479, 419.
46. Touet, J.; Baudouin, S.; Brown, E. Tetrahedron: Asymmetry 1992, 3, 587-590.