Catalytic asymmetric synthesis of optically active atropisomeric anilides through enantioselective N-allylation with chiral Pd-tol-BINAP catalyst

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8682-8684

  Kitagawa, Osamu ^a   Kohriyama, Mitsuteru ^a   Taguchi, Takeo ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL YIELDS;

CATALYSIS; DERIVATIVES; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ANILIDE;

ALLYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; STEREOCHEMISTRY;

EID: 0037195764     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0264271     Document Type: Article

References (41)

1. (a) Bock, L. H.; Adams, R. J. Am. Chem. Soc. 1931, 53, 374.
2. (b) Kashima, C.; Katoh, A. J. Chem. Soc., Perkin Trans. 1 1980, 1599.
3. (c) Roussel, C.; Adjimi, M.; Chemlal, A.; Djafri, A. J. Org. Chem. 1988, 53, 5076.
4. (d) Kawamoto, T.; Tomishima, M.; Yoneda, F.; Hayami, J. Tetrahedron Lett. 1992, 33, 3169.
5. (e) Mannschreck, A.; Koller, H.; Stuhler, G.; Davies, M. A.; Traber, J. Eur. J. Med. Chem. Chim. Ther. 1984, 19, 381.
6. 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.
7. Curran, D. P.; Qi, H.; Geib, S. J.; DeMello, N. C. J. Am. Chem. Soc. 1994, 116, 3131.
8. (a) Kishikawa, K.; Tsuru, I.; Kohomoto, S.; Yamamoto, M.; Yamada, K. Chem. Lett. 1994, 1605.
9. (b) Hughes, A. D.; Price, D. A.; Shishkin, O.; Simpkins, N. S. Tetrahedron Lett. 1996, 37, 7607.
10. (c) Bach, T.; Schröder, J.; Harms, K. Tetrahedron Lett. 1999, 40, 9003.
11. Kitagawa, O.; Izawa, H.; Taguchi, T.; Shiro, M. Tetrahedron Lett. 1997, 38, 4447.
12. (a) Hughes, A. D.; Simpkins, N. S. Synlett 1998, 967.
13. (b) Hughes, A. D.; Price, D. A.; Simpkins, N. S. J. Chem. Soc., Perkin Trans. 1 1999, 1295.
14. (c) Kondo, K.; Fujita, H.; Suzuki, T.; Murakami, Y. Tetrahedron Lett. 1999, 40, 5577.
15. (d) Curran, D. P.; Liu, W.; Chen, C. H. J. Am. Chem. Soc. 1999, 121, 11012.
16. (e) Shimizu, K. D.; Freyer, H. O.; Adams, R. D. Tetrahedron Lett. 2000, 41, 5431,
17. (f) Kondo, K.; Iida, T.; Fujita, H.; Suzuki, T.; Yamaguchi, K.; Murakami, Y. Tetrahedron 2000, 56, 8883.
18. (g) Godfrey, C. R. A.; Simpkins, N. S.; Walker, M. D. Synlett 2000, 388.
19. (h) Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130.
20. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
21. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
22. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
23. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
24. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
25. Our papers on the preparation of optically active atropisomeric anilides through other methods: (a) Kitagawa, O.; Izawa, H.; Sato, K.; Dobashi, A.; Taguchi, T.; Shiro, M. J. Org. Chem. 1998, 63, 2634. (b) Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 1999, 40, 1949 (Corrigendum: Fujita, M.; Kitagawa, O.; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 4997). (c) Kitagawa, O.; Momose, S.; Fushimi, Y.; Taguchi, T. Tetrahedron Lett, 1999, 40, 8827. (d) Fujita, M.; Kitagawa, O.; Yamada, Y.; Izawa, H.; Hasegawa, H.; Taguchi, T. J. Org. Chem. 2000, 65, 1108. (e) Kitagawa, O.; Fujita, M.; Kohriyama, M.; Hasegawa, H.; Taguchi, T. Tetrahedron Lett. 2000, 41, 8539.
26. (a) Hata, T.; Koide, H.; Taniguchi, N.; Uemura, M. Org. Lett. 2000, 2, 1907.
27. (b) Koide, H.; Hata, T.; Uemura, H. J. Org. Chem. 2002, 67, 1929.
28. N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the synthesis of optically active forms of these compounds has been reported by several groups, while there is no report on their catalytic asymmetric synthesis except for kinetic resolution. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556. (c) Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266. (d) Rios, R.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10272.
29. N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the synthesis of optically active forms of these compounds has been reported by several groups, while there is no report on their catalytic asymmetric synthesis except for kinetic resolution. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556. (c) Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266. (d) Rios, R.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10272.
30. N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the synthesis of optically active forms of these compounds has been reported by several groups, while there is no report on their catalytic asymmetric synthesis except for kinetic resolution. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556. (c) Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266. (d) Rios, R.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10272.
31. N,N-Dialkyl 2,6-disubstituted aromatic amides are also known to exist as stable nonbiaryl atropisomeric compounds at room temperature. Recently, the synthesis of optically active forms of these compounds has been reported by several groups, while there is no report on their catalytic asymmetric synthesis except for kinetic resolution. (a) Thayumanavan, S.; Beak, P.; Curran, D. P. Tetrahedron Lett. 1996, 37, 2899. (b) Clayden, J.; Lai, L. W. Angew. Chem., Int. Ed. 1999, 38, 2556. (c) Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266. (d) Rios, R.; Jimeno, C.; Carrol, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2002, 124, 10272.
32. For reviews on catalytic asymmetric allylation with a chiral π-allylpalladium complex see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (c) Williams, J. M. Synlett 1996, 705.
33. For reviews on catalytic asymmetric allylation with a chiral π-allylpalladium complex see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (c) Williams, J. M. Synlett 1996, 705.
34. For reviews on catalytic asymmetric allylation with a chiral π-allylpalladium complex see: (a) Hayashi, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1994; pp 325-365. (b) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395. (c) Williams, J. M. Synlett 1996, 705.
35. (a) Trost, B. M.; Radinov, R.; Grenzer, E. M. J. Am. Chem. Soc. 1997, 119, 7879.
36. (b) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759.
37. Hayashi, T.; Kanehira, K.; Hagihara, T.; Kumada, M. J. Org. Chem. 1988, 53, 113.
38. Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336.
39. (a) Noyori, Y.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
40. (b) Mashima, K.; Kusano, K.; Sato, N.; Matsumura, Y.; Nozaki, K.; Kumobayashi, H.; Sayo, N.; Hori, Y.; Ishizuka, T.; Akutagawa, S.; Takaya, H. J. Org. Chem. 1994, 59, 3064.
41. The reaction with -BINAP gave the 1a of 33% ee.