Asymmetric Hetero Diels-Alder Reaction Catalyzed by Chiral Ytterbium(III) Phosphate {Yb[(R)-(-)-BNP]3}: Remarkable Ligand Effect on the Enantioselectivity

Synlett

Volumn 1997, Issue 1, 1997, Pages 79-80

  Hanamoto, T ^a   Furuno, H ^a   Sugimoto, Y ^a   Inanaga, J ^a  

^a KYUSHU UNIVERSITY   (Japan)

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Indexed keywords

EID: 0002296924     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-718     Document Type: Article

References (23)

1. Asymmetric reactions with isolable chiral rare earth metal complexes. (a) Sasai, H.; Arai, S.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194, and references cited therein.
2. (b) Yokomatsu, Y.; Yamagishi, T.; Shibuya, S. Tetrahedron Asymm. 1993, 4, 1783.
3. (c) Bednarski, M.; Maring, C.; Danishefsky, S. Tetrahedron Lett. 1983, 24, 3451.
4. Asymmetric reactions with chiral rare earth metal complexes prepared in situ. (a) Mikami, K.; Kotera, O.; Motoyama, Y.; Sakaguchi, H. Synlett. 1995, 975.
5. (b) Kobayashi, S.; Ishitani, H. J. Am. Chem. Soc. 1994, 116, 4083.
6. (c) Kobayashi, S.; Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett. 1994, 35, 6325.
7. (d) Kobayashi, S.; Araki, M.; Hachiya, I. J. Org. Chem. 1994, 59, 3758.
8. (e) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Tetrahedron Lett. 1993, 34, 4535.
9. 21=-395° (c=1.00, THF).
10. Inanaga, J.; Sugimoto, Y.; Hanamoto, T. New J. Chem. 1995, 19, 707.
11. A part of the work was presented at the 1995 International Chemical Congress of Basin Societies, Hawaii, December 1995.
12. 7g (HPLC, Chiralcel OD, hexane:i-PrOH=9:1).
13. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
14. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
15. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
16. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
17. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
18. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
19. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
20. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
21. Previous examples of this type reaction: (a) Reference 1c. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310. (c) Faller, J. W.; Smart, C. J. Tetrahedron Lett. 1989, 30, 1189. (d) Togni, A. Organometallics, 1990, 9, 3106. (e) Togni, A.; Pastor, S, D. Chirality, 1991, 3, 331. (f) Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951. (g) Gao, Q.; Ishihara, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979. (h) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (i) Keck, G. E.; Li, X-Y.; Krishnamurthy, D. J. Org. Chem. 1995, 60, 5998.
22. When the present reaction was carried out at 3°C, the enantiomeric excess increased to 91% ee (79% chemical yield), however, the reaction at a lower temperature no longer improved the ee (e.g., at -25°C; 91% ee, 45% chemical yield).
23. It provided a 91% isolated yield of product with 82% ee.