A catalytic asymmetric 1,3-dipolar cycloaddition of nitrones to allyl alcohol

Chemistry Letters

Volumn , Issue 5, 2001, Pages 468-469

  Ding, Xia ^a   Taniguchi, Katsumi ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035533876     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.468     Document Type: Article

References (19)

1. K. V. Gothelf and K. A. Jørgensen, Chem. Commun., 2000, 1449; K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 98, 863 (1998).
2. K. V. Gothelf and K. A. Jørgensen, Chem. Commun., 2000, 1449; K. V. Gothelf and K. A. Jørgensen, Chem. Rev., 98, 863 (1998).
3. M. Kawamura and S. Kobayashi, Tetrahedron Lett., 40, 3213 (1999); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, J. Org. Chem., 64, 5017 (1999); S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998); S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 120, 5840 (1998).
4. M. Kawamura and S. Kobayashi, Tetrahedron Lett., 40, 3213 (1999); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, J. Org. Chem., 64, 5017 (1999); S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998); S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 120, 5840 (1998).
5. M. Kawamura and S. Kobayashi, Tetrahedron Lett., 40, 3213 (1999); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, J. Org. Chem., 64, 5017 (1999); S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998); S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 120, 5840 (1998).
6. M. Kawamura and S. Kobayashi, Tetrahedron Lett., 40, 3213 (1999); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, J. Org. Chem., 64, 5017 (1999); S. Kanemasa, Y. Oderaotoshi, J. Tanaka, and E. Wada, J. Am. Chem. Soc., 120, 12355 (1998); S. Kobayashi and M. Kawamura, J. Am. Chem. Soc., 120, 5840 (1998).
7. Other types of asymmetric 1,3-dipolar cycloaddition of nitrones: K. B. Jensen, M. Roberson, and K. A. Jørgensen, J. Org. Chem., 65, 9080 (2000); W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, J. Am. Chem. Soc., 122, 9874 (2000); K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Jørgensen, J. Am. Chem. Soc., 121, 3845 (1999); K. B. Jensen, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 64, 2353 (1999);
8. Other types of asymmetric 1,3-dipolar cycloaddition of nitrones: K. B. Jensen, M. Roberson, and K. A. Jørgensen, J. Org. Chem., 65, 9080 (2000); W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, J. Am. Chem. Soc., 122, 9874 (2000); K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Jørgensen, J. Am. Chem. Soc., 121, 3845 (1999); K. B. Jensen, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 64, 2353 (1999);
9. Other types of asymmetric 1,3-dipolar cycloaddition of nitrones: K. B. Jensen, M. Roberson, and K. A. Jørgensen, J. Org. Chem., 65, 9080 (2000); W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, J. Am. Chem. Soc., 122, 9874 (2000); K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Jørgensen, J. Am. Chem. Soc., 121, 3845 (1999); K. B. Jensen, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 64, 2353 (1999);
10. Other types of asymmetric 1,3-dipolar cycloaddition of nitrones: K. B. Jensen, M. Roberson, and K. A. Jørgensen, J. Org. Chem., 65, 9080 (2000); W. S. Jen, J. J. M. Wiener, and D. W. C. MacMillan, J. Am. Chem. Soc., 122, 9874 (2000); K. B. Simonsen, P. Bayón, R. G. Hazell, K. V. Gothelf, and K. A. Jørgensen, J. Am. Chem. Soc., 121, 3845 (1999); K. B. Jensen, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 64, 2353 (1999);
11. J. P. G. Seerden, M. M. M. Boeren, and H. W. Scheeren, Tetrahedron, 53, 11843 (1997).
12. Y. Yoshida, Y. Ukaji, S. Fujinami, and K. Inomata, Chem. Lett., 1998, 1023.
13. M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett.. 1996, 455.
14. Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847.
15. Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547.
16. The stereochemistry of the nitrones 2a,d was determined by NOE analysis to be Z.
17. S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 3390 (1997).
18. 4b) were not so effective. Amine N-oxides might be able to coordinate more effectively to zinc metal like nitrones to avoid the unfavorable aggregation.
19. NOE established the cis relationship of cycloadducts 3a,d as shown below. (formula presented)