Novel cerium(III)-(R)-BNP complex as a storable chiral Lewis acid catalyst for the enantioselective Hetero-Diels-Alder reaction

Chemistry Letters

Volumn 32, Issue 7, 2003, Pages 608-609

  Hayano, Tetsuji ^a   Sakaguchi, Toshiaki ^a   Furuno, Hiroshi ^a   Ohba, Masaaki ^a   Okawa, Hisashi ^a   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CERIUM; LEWIS ACID; PYRAN DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 0141540676     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.608     Document Type: Article

References (22)

1. For recent reviews, see: a) J. Inanaga, H. Furuno, and T. Hayano, Chem. Rev., 102, 2211 (2002). b) S. Kobayashi, M. Sugiura, H. Kitagawa, and W. W.-L. Lam, Chem. Rev., 102, 2227 (2002). c) K. Mikami, M. Terada, and H. Matsuzawa, Angew. Chem., Int. Ed. Engl., 41, 3554 (2002).
2. For recent reviews, see: a) J. Inanaga, H. Furuno, and T. Hayano, Chem. Rev., 102, 2211 (2002). b) S. Kobayashi, M. Sugiura, H. Kitagawa, and W. W.-L. Lam, Chem. Rev., 102, 2227 (2002). c) K. Mikami, M. Terada, and H. Matsuzawa, Angew. Chem., Int. Ed. Engl., 41, 3554 (2002).
3. For recent reviews, see: a) J. Inanaga, H. Furuno, and T. Hayano, Chem. Rev., 102, 2211 (2002). b) S. Kobayashi, M. Sugiura, H. Kitagawa, and W. W.-L. Lam, Chem. Rev., 102, 2227 (2002). c) K. Mikami, M. Terada, and H. Matsuzawa, Angew. Chem., Int. Ed. Engl., 41, 3554 (2002).
4. For the enantioselective reactions using chiral cerium catalysts prepared in situ, see: a) S. Kobayashi, T. Hamada, S. Nagayama, and K. Manabe, Org. Lett., 3, 165 (2001). b) G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori, and M. Zema, Tetrahedron, 57, 10203 (2001).
5. For the enantioselective reactions using chiral cerium catalysts prepared in situ, see: a) S. Kobayashi, T. Hamada, S. Nagayama, and K. Manabe, Org. Lett., 3, 165 (2001). b) G. Desimoni, G. Faita, S. Filippone, M. Mella, M. G. Zampori, and M. Zema, Tetrahedron, 57, 10203 (2001).
6. a) J. Inanaga, Y. Sugimoto, and T. Hanamoto, New J. Chem., 19, 707 (1995).
7. b) T. Hanamoto, H. Furuno, Y. Sugimoto, and J. Inanaga, Synlett, 1997, 79.
8. c) H. Furuno, T. Hanamoto, Y. Sugimoto, and J. Inanaga, Org. Lett., 2, 49 (2000).
9. 3-catalyzed asymmetric Michael addition of O-alkylhydroxylamines to conjugated enones, see: a) H. Sugihara, K. Daikai, X. L. Jin, H. Furuno, and J. Inanaga, Tetrahedron Lett., 43, 2735 (2002). b) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanaga, Tetrahedron, 58, 8321 (2002). c) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanga, Tetrahedron, 59, 877 (2003).
10. 3-catalyzed asymmetric Michael addition of O-alkylhydroxylamines to conjugated enones, see: a) H. Sugihara, K. Daikai, X. L. Jin, H. Furuno, and J. Inanaga, Tetrahedron Lett., 43, 2735 (2002). b) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanaga, Tetrahedron, 58, 8321 (2002). c) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanga, Tetrahedron, 59, 877 (2003).
11. 3-catalyzed asymmetric Michael addition of O-alkylhydroxylamines to conjugated enones, see: a) H. Sugihara, K. Daikai, X. L. Jin, H. Furuno, and J. Inanaga, Tetrahedron Lett., 43, 2735 (2002). b) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanaga, Tetrahedron, 58, 8321 (2002). c) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi, Y. Z. Jin, H. Furuno, and J. Inanga, Tetrahedron, 59, 877 (2003).
12. B.
13. For some recent examples of the highly efficient catalytic asymmetric hetero-Diels-Alder reaction with 3, see: a) S. Kii, T. Hashimoto, and K. Maruoka, Synlett, 2002, 937. b) B. Wang, X. Feng, Y. Huang, H. Liu, X. Cui, and Y. Jiang, J. Org. Chem., 67, 2175 (2002). c) J. Long, J. Hu, X. Shen, B. Ji, and K. Ding, J. Am. Chem. Soc., 124, 10 (2002).
14. For some recent examples of the highly efficient catalytic asymmetric hetero-Diels-Alder reaction with 3, see: a) S. Kii, T. Hashimoto, and K. Maruoka, Synlett, 2002, 937. b) B. Wang, X. Feng, Y. Huang, H. Liu, X. Cui, and Y. Jiang, J. Org. Chem., 67, 2175 (2002). c) J. Long, J. Hu, X. Shen, B. Ji, and K. Ding, J. Am. Chem. Soc., 124, 10 (2002).
15. For some recent examples of the highly efficient catalytic asymmetric hetero-Diels-Alder reaction with 3, see: a) S. Kii, T. Hashimoto, and K. Maruoka, Synlett, 2002, 937. b) B. Wang, X. Feng, Y. Huang, H. Liu, X. Cui, and Y. Jiang, J. Org. Chem., 67, 2175 (2002). c) J. Long, J. Hu, X. Shen, B. Ji, and K. Ding, J. Am. Chem. Soc., 124, 10 (2002).
16. M. Bednarski, C. Maring, and S. Danishefsky, Tetrahedron Lett., 24, 3451 (1983).
17. For some reviews on the positive nonlinear effect, see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986). b) N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1988). c) D. G. Blackmond, Acc. Chem. Res., 33, 402 (2000). d) R. Noyori, S. Suga, H. Oka, and M. Kitamura, Chem. Rec., 1, 85 (2001). e) H. B. Kagan, Synlett, 2001, 888.
18. For some reviews on the positive nonlinear effect, see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986). b) N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1988). c) D. G. Blackmond, Acc. Chem. Res., 33, 402 (2000). d) R. Noyori, S. Suga, H. Oka, and M. Kitamura, Chem. Rec., 1, 85 (2001). e) H. B. Kagan, Synlett, 2001, 888.
19. For some reviews on the positive nonlinear effect, see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986). b) N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1988). c) D. G. Blackmond, Acc. Chem. Res., 33, 402 (2000). d) R. Noyori, S. Suga, H. Oka, and M. Kitamura, Chem. Rec., 1, 85 (2001). e) H. B. Kagan, Synlett, 2001, 888.
20. For some reviews on the positive nonlinear effect, see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986). b) N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1988). c) D. G. Blackmond, Acc. Chem. Res., 33, 402 (2000). d) R. Noyori, S. Suga, H. Oka, and M. Kitamura, Chem. Rec., 1, 85 (2001). e) H. B. Kagan, Synlett, 2001, 888.
21. For some reviews on the positive nonlinear effect, see: a) C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc., 108, 2353 (1986). b) N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1988). c) D. G. Blackmond, Acc. Chem. Res., 33, 402 (2000). d) R. Noyori, S. Suga, H. Oka, and M. Kitamura, Chem. Rec., 1, 85 (2001). e) H. B. Kagan, Synlett, 2001, 888.
22. The ICP-MS data for 6: Ce, 8.4; P, 5.8 (the calculated Ce/P ratio is 1:3.1). For 7: Ce, 11; P, 7.2 (Ce/P = 1:3.0).