Asymmetric synthesis of axially chiral anilides by enantiotopic lithiation of tricarbonyl(N-methyl-N-acyl-2,6-dimethylanilide)chromium complex

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1907-1910

  Hata, Takeshi ^a   Koide, Hiroshige ^a   Taniguchi, Nobukazu ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

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Indexed keywords

EID: 0001163250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0001057     Document Type: Article

References (27)

1. Some representative axially chiral naphth-or benzamides: (a) Clayden, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 949.
2. (b) Clayden, J.; Westlund, N.; Wilson, F. X. Tetrahedron Lett. 1999, 40, 3329.
3. (c) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556.
4. (d) Ahmed, A.; Bragg, R. A.; Clayden, J.; Lai, L. W. McCarthy, C.; Pink, J. H.; Westlund, N.; Yasin, S. A. Tetrahedron 1998, 54, 13277.
5. (e) Mikata, Y.; Hayashi, K.; Mizukami, K.; Matsumoto, S.; Yano, S.; Yamazaki, N.; Ohno, A. Tetrahedron Lett. 2000, 41, 1035.
6. Axially chiral anilide: (a) Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
7. (b) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
8. (c) Kishikawa, K.; Tsuru, I.; Kohmoto, S.; Yamamoto, M.; Yamada, K. Chem. Lett. 1994, 1605.
9. (d) Curran, D. P.; Hale, G. R.; Geib, S. J.; Balog, A.; Cass, Q. B.; Degani, A. L. G.; Hernandes, M. Z.; Freita, L. C. G. Tetrahedron: Asymmetry 1997, 8, 3955.
10. (a) Cass, Q.; Degani, A. L. G.; Tiritan, M. E.; Matlin, S. A. Curran, D. P.; Balog, A. Chirality 1997, 2, 9.
11. (b) Cuyegkeng, M. A.; Mannschreck, A. Chem. Ber. 1987, 120, 803.
12. (c) Pirkle, W. H.; Welch, C. J.; Zych, A. J. J. Chromatogr. 1993, 643, 101.
13. (d) Kondo, K.; Fukita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
14. (e) 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.
15. (a) Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
16. (b) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T. J. Org. Chem. 1998, 63, 2634.
17. (c) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949.
18. (d) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967.
19. (a) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949.
20. (b) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108.
21. (c) Dai, X.; Wong, A.; Virgil, S. C. J. Org. Chem. 1998, 63, 2597.
22. (d) Dai, X.; Virgil, S. Tetrahedron Lett. 1999, 40, 1245.
23. (a) Koide, H.; Uemura, M. Chem. Commun. 1998, 2483.
24. (b) Koide, H. Uemura, M. Chirality, in press.
25. The trans-rotamer in the chromium-complexed anilide 2 is in sharp contrast to the tricarbonylchromium-free N-methyl-N-acylanilides, in which N-methyl is preferentially cis-oriented to the carbonyl oxygen in both the crystalline state and solution. See 3e and following references: (a) Itai, A.; Toriumi, Y.; Tomioka, N.; Kagechika, H.; Azumaya, I.; Shudo, K. Tetrahedron Lett. 1989, 30, 6177.
26. (b) Itai, A.; Toriumi, Y.; Saito, S.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1992, 114, 10649.
27. (c) Azumaya, I.; Yamaguchi, K.; Okamoto, I.; Kagechika, H.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 9083.