β-isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of imines

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3103-3105

  Kawahara, Sakie ^a   Nakano, Ayako ^a   Esumi, Tomoyuki ^a   Iwabuchi, Yoshiharu ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,1,3,3,3 HEXAFLUOROISOPROPYL ACRYLATE; ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; BETA ISOCUPREIDINE; CHEMICAL COMPOUND; ESTER DERIVATIVE; HYDROGEN; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND;

EID: 0141743697     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035102j     Document Type: Article

References (31)

1. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
2. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
3. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
4. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
5. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
6. For reviews: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653. (b) Basavaiah, D.; Darma Rao, P.; Suguna Hyma, R. Tetrahedron 1996, 52, 8001. (c) Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; Wiley: New York, 1997; Vol. 51, p 201. (d) Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049. (e) Iwabuchi, Y.; Hatakeyama, S. J. Synth. Org. Chem. Jpn. 2002, 60, 4. (f) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811.
7. We recently found that this compound was named β-isocupreidine in the early study of cinchona alkaloids: Suszko, J. Rocz. Chem. 1935, 15, 209. For structural elucidation: Dega-Szafran, Z. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1966, 14, 529.
8. We recently found that this compound was named β-isocupreidine in the early study of cinchona alkaloids: Suszko, J. Rocz. Chem. 1935, 15, 209. For structural elucidation: Dega-Szafran, Z. Bull. Acad. Pol. Sci., Ser. Sci. Chim. 1966, 14, 529.
9. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219.
10. (a) Iwabuchi, Y.; Furukawa, M.; Esumi, T.; Hatakeyama, S. Chem. Commun. 2001, 2030.
11. (b) Iwabuchi, Y.; Sugihara, T.; Esumi, T.; Hatakeyama, S. Tetrahedron Lett. 2001, 42, 7867.
12. For recent studies on Baylis-Hillman reaction of imines: (a) Richter, H. ; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (b) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577. (c) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329. (d) Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2002, 43, 4305.
13. For recent studies on Baylis-Hillman reaction of imines: (a) Richter, H. ; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (b) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577. (c) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329. (d) Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2002, 43, 4305.
14. For recent studies on Baylis-Hillman reaction of imines: (a) Richter, H. ; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (b) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577. (c) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329. (d) Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2002, 43, 4305.
15. For recent studies on Baylis-Hillman reaction of imines: (a) Richter, H. ; Jung, G. Tetrahedron Lett. 1998, 39, 2729. (b) Aggarwal, V. K.; Castro, A. M. M.; Mereu, A.; Adams, H. Tetrahedron Lett. 2002, 43, 1577. (c) Balan, D.; Adolfsson, H. J. Org. Chem. 2002, 67, 2329. (d) Azizi, N.; Saidi, M. R. Tetrahedron Lett. 2002, 43, 4305.
16. Shi, M.; Xu, Y.-M. Angew. Chem., Int. Ed. 2002, 41, 4507.
17. Balan, D.; Adolfsson, H. Tetrahedron Lett. 2003, 44, 2521.
18. Imines were prepared according to the following procedures. For 1a and 1b: Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 40, 2271. For 1c: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. For 1d: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. For 1e and 1f: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. For 1g-k: Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
19. Imines were prepared according to the following procedures. For 1a and 1b: Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 40, 2271. For 1c: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. For 1d: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. For 1e and 1f: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. For 1g-k: Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
20. Imines were prepared according to the following procedures. For 1a and 1b: Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 40, 2271. For 1c: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. For 1d: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. For 1e and 1f: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. For 1g-k: Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
21. Imines were prepared according to the following procedures. For 1a and 1b: Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 40, 2271. For 1c: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. For 1d: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. For 1e and 1f: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. For 1g-k: Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
22. Imines were prepared according to the following procedures. For 1a and 1b: Xue, S.; Yu, S.; Deng, Y.; Wulff, W. D. Angew. Chem., Int. Ed. 2001, 40, 2271. For 1c: Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555. For 1d: Gizecki, P.; Dhal, R.; Toupet, L.; Dujardin, G. Org. Lett. 2000, 2, 585. For 1e and 1f: Georg, G. I.; Harriman, G. C. B.; Peterson, S. A. J. Org. Chem. 1995, 60, 7366. For 1g-k: Yamada, K.; Harwood, S. J.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 3504.
23. (a) Li, G.; Wei, H.-X.; Whittlesey, B. R.; Batrice, N. N. J. Org. Chem. 1999, 64, 1061.
24. (b) Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207.
25. Kobayashi, K.; Okamoto, T.; Oida, T.; Tanimoto, S. Chem. Lett. 1986, 2031.
26. 7} to be (R)-enriched. Shi et al. did not clearly mention how they deduced the absolute configuration. Adolfsson et al. determined it on the basis of the specific rotation reported by Shi et al.
27. (a) Ramage, R.; Hopton, D.; Parrott, M. J. J. Chem. Soc., Perkin Trans. 1 1984, 1357.
28. (b) Yamada, K.; Moll, G.; Shibasaki, M. Synlett 2001, 980.
29. (c) Tsuritani, N.; Yamada, K.; Yoshikawa, N.; Shibasaki, M. Chem. Lett. 2002, 276.
30. (d) Cantrill, A. A.; Osborn, H. M. I.; Sweeney, J. Tetrahedron 1998, 54, 2181.
31. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983; pp 252-257.