Synthesis of optically active 5-substituted-2-pyrrolidinone derivatives having atropisomeric structure and 3,5-cis-selective reaction of their enolates with electrophiles

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1108-1114

  Fujita, Masao ^a   Kitagawa, Osamu ^a   Yamada, Yoichiro ^a   Izawa, Hirotaka ^a   Hasegawa, Hiroshi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE;

ARTICLE; CHIRALITY; CIS TRANS ISOMERISM; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034712335     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991578y     Document Type: Article

References (38)

1. (a) Kashima, C.; Katoh, A.; J. Chem. Soc., Perkin Trans. 1 1980, 1599.
2. (b) Roussel, C.; Adjimi, M.; Chemlal, A.; Djafri, A. J. Org. Chem. 1988, 53, 5076.
3. (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131-3132.
4. (b) Kishikawa, K.; Tsuru, I.; Kohmoto, S.; Yamamoto, M.; Yamada, K. Chem Lett. 1994, 1605.
5. (c) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
6. (d) Clayden, J.; Angew. Chem., Int. Ed. Engl. 1997, 36, 949.
7. (a) Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
8. (b) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634.
9. Recently, Simpkins et al. also reported the synthesis of optically active N-(o-tert-butylphenyl)propanamide (93% ee) in accordance with our optical resolution method (ref 2). (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295. On the other hand, the synthesis of optically pure forms of atropisomeric amides and imides through the optical resolution using chiral chromatography has been reported by two groups, while the absolute configuration of these atropisomeric compounds has not yet been determined. (c) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955. (d) Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
10. Recently, Simpkins et al. also reported the synthesis of optically active N-(o-tert-butylphenyl)propanamide (93% ee) in accordance with our optical resolution method (ref 2). (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295. On the other hand, the synthesis of optically pure forms of atropisomeric amides and imides through the optical resolution using chiral chromatography has been reported by two groups, while the absolute configuration of these atropisomeric compounds has not yet been determined. (c) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955. (d) Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
11. Recently, Simpkins et al. also reported the synthesis of optically active N-(o-tert-butylphenyl)propanamide (93% ee) in accordance with our optical resolution method (ref 2). (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295. On the other hand, the synthesis of optically pure forms of atropisomeric amides and imides through the optical resolution using chiral chromatography has been reported by two groups, while the absolute configuration of these atropisomeric compounds has not yet been determined. (c) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955. (d) Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
12. Recently, Simpkins et al. also reported the synthesis of optically active N-(o-tert-butylphenyl)propanamide (93% ee) in accordance with our optical resolution method (ref 2). (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295. On the other hand, the synthesis of optically pure forms of atropisomeric amides and imides through the optical resolution using chiral chromatography has been reported by two groups, while the absolute configuration of these atropisomeric compounds has not yet been determined. (c) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freitas, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955. (d) Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
13. (a) Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 51, 3140.
14. (b) Ohta, T.; Hosoi, A.; Nozoe, S. Tetrahedron Lett. 1988, 29, 329.
15. (c) Baldwin, J. E.; Miranda, T.; Moloney, M. G.; Hokelek, T. Tetrahedron 1989, 45, 7459.
16. (d) Hon, Y.; Chang, Y.; Gong, M. Heterocycles 1990, 31, 191.
17. (e) Baldwin, J. E.; Moloney, M. G.; Shim, S. B. Tetrahedron Lett. 1991, 32, 1379.
18. (f) Armstrong, R. W.; DeMattei, J. A. Tetrahedron Lett. 1991, 32, 5749.
19. (g) Langlois, N.; Rojas, A.; Tetrahedron Lett. 1993, 34, 2477.
20. (h) Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Escribano, A.; Sanchez-Ferrando, F. Tetrahedron 1993, 49, 8665.
21. (i) Nagasaka, T.; Imai, T. Chem. Pharm. Bull. 1995, 43, 1081.
22. (j) Charrier, J. D.; Duffy, J. E. S.; Hitchcock, P. B.; Young, D. W. Tetrahedron Lett. 1998, 39, 2199.
23. (k) Zhang, R.; Brownewell, F.; Madalengoitia, J. S. Tetrahedron Lett. 1999, 40, 2707.
24. For review: (l) Nàjera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245. See also ref 6b.
25. Papers in relation to the origin of 3,5-trans-selectivity: (a) Seebach, D.; Maetzke, T.; Petter, W.; Klotzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781. (b) Meyers, A. I.; Seefeld, M. A.; Bruce, A. L.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565. (c) Ando, K.; Green, N. S.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 5334.
26. Papers in relation to the origin of 3,5-trans-selectivity: (a) Seebach, D.; Maetzke, T.; Petter, W.; Klotzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781. (b) Meyers, A. I.; Seefeld, M. A.; Bruce, A. L.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565. (c) Ando, K.; Green, N. S.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 5334.
27. Papers in relation to the origin of 3,5-trans-selectivity: (a) Seebach, D.; Maetzke, T.; Petter, W.; Klotzer, B.; Plattner, D. A. J. Am. Chem. Soc. 1991, 113, 1781. (b) Meyers, A. I.; Seefeld, M. A.; Bruce, A. L.; Blake, J. F. J. Am. Chem. Soc. 1997, 119, 4565. (c) Ando, K.; Green, N. S.; Li, Y.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 5334.
28. Moderate 3.5-cis-selectivity (cis/trans = 5) has been observed in the reaction of bicyclic lactam enolate with a small electrophile such as MeI, while under the same conditions, the reaction with other electrophiles such as allyl bromide and benzyl bromide proceeded in a nonselective manner or with low 3,5-trans-selectivity. See refs 5f, 5j, and 5k.
29. Preliminary communication of this work: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949.
30. It has been reported that nitrogen of amide Li-enolates is completely tetrahedralized. (a) Laube, T.; Dunitz, J. D. Seebach, D. Helv. Chim. Acta 1985, 68, 1373. (b) Bauer, W.; Laube, T.; Seebach, D. Chem. Ber. 1985, 118, 764.
31. It has been reported that nitrogen of amide Li-enolates is completely tetrahedralized. (a) Laube, T.; Dunitz, J. D. Seebach, D. Helv. Chim. Acta 1985, 68, 1373. (b) Bauer, W.; Laube, T.; Seebach, D. Chem. Ber. 1985, 118, 764.
32. The stereochemistries of the products were determined on the basis of NOE experiments.
33. The stereochemistries of cis- and trans-5b were determined after conversion to benzoate 6b, because cis- and trans-6b can be easily separated in comparison with cis- and trans-5b (Scheme 6).
34. 1H NMR.
35. Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37.
36. Separation of the cis- and trans-13 was easily carried out in comparison with that of cis- and trans-12.
37. Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
38. Nemoto, H.; Nagai, M.; Fukumoto, K.; Kametani, T. J. Org. Chem. 1985, 50, 2764.