Lanthanide triflate-catalyzed three-component coupling reactions of aldehydes, hydroxylamines, and alkenes leading to isoxazolidine derivatives

Chemistry Letters

Volumn , Issue 10, 1997, Pages 1039-1040

  Kobayashi, Shu ^a   Akiyama, Ryo ^a   Kawamura, Mikako ^a   Ishitani, Haruro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000923659     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (44)

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10. Recently, multiple-component reactions have been recognized as one of the most efficient methods for library construction. I. Ugi, A. Dömling, and W. Hörl, Endeavour, 18, 115 (1994); R. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res., 29, 123 (1996).
11. Recently, multiple-component reactions have been recognized as one of the most efficient methods for library construction. I. Ugi, A. Dömling, and W. Hörl, Endeavour, 18, 115 (1994); R. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, and T. A. Keating, Acc. Chem. Res., 29, 123 (1996).
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18. S. Kobayashi, M. Araki, and M. Yasuda, Tetrahedron Lett., 36, 5773 (1995); S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, I. Hachiya, S. Suzuki, and M. Moriwaki, Tetrahedron Lett., 37, 2809 (1996); S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu, and A. R. Katritzky, Tetrahedron Lett., 37, 3731 (1996); S. Kobayashi, M. Moriwaki, R. Akiyama, S. Suzuki, and I. Hachiya, Tetrahedron Lett., 37, 7783 (1996); S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron Lett., 37, 9221 (1996); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997).
19. S. Kobayashi, M. Araki, and M. Yasuda, Tetrahedron Lett., 36, 5773 (1995); S. Kobayashi and H. Ishitani, J. Chem. Soc., Chem. Commun., 1995, 1379; S. Kobayashi, I. Hachiya, S. Suzuki, and M. Moriwaki, Tetrahedron Lett., 37, 2809 (1996); S. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu, and A. R. Katritzky, Tetrahedron Lett., 37, 3731 (1996); S. Kobayashi, M. Moriwaki, R. Akiyama, S. Suzuki, and I. Hachiya, Tetrahedron Lett., 37, 7783 (1996); S. Kobayashi, S. Nagayama, and T. Busujima, Tetrahedron Lett., 37, 9221 (1996); S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997).
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24. S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., in press.
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26. H. Ishitani, S. Nagayama, and S. Kobayashi, J. Org. Chem., 61, 1902 (1996).
27. Unpublished. Cf. S. Minakata, T. Ezoe, R. Ilhyong, M. Komatsu, and Y. Ohshiro, the 72nd Annual Meeting of the Chemical Society of Japan, Tokyo, 1997, 2F3 37.
28. 4-9
29. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi, I. Hachiya, and Y. Yamanoi, Bull. Chem. Soc. Jpn., 67, 2342 (1994).
30. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi, I. Hachiya, and Y. Yamanoi, Bull. Chem. Soc. Jpn., 67, 2342 (1994).
31. 3, etc. and found that they were also effective. Full data will be reported in due course.
32. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
33. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
34. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
35. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
36. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
37. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
38. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
39. As for asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using chiral catalysts, Review: M. Frederickson, Tetrahedron, 53, 403 (1997); See also, K. V. Gothelf and K. A. Jørgensen, J. Org. Chem., 59, 5687 (1994); J.-P. G. Seerden, A. W. A. Scholte op Reimer, and H. W. Scheeren, Tetrahedron Lett., 35, 4419 (1994); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron Asym., 6, 1441 (1995); D. Seebach, R. E. Marti, and T. Hintermann, Helv. Chim. Acta, 79, 1710 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); K. B. Jensen, K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 62, 2471 (1997), and references cited therein. Cf. K. Narasaka, N. Iwasawa, M. Inoue, T. Yamada, M. Nakashima, and J. Sugimori, J. Am. Chem. Soc., 111, 5340 (1989).
40. S. Kobayashi and H. Ishitani, J. Am. Chem. Soc., 116, 4083 (1994); S. Kobayashi, M. Araki, and I. Hachiya, J. Org. Chem., 59, 3758 (1994); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996), and references cited therein.
41. S. Kobayashi and H. Ishitani, J. Am. Chem. Soc., 116, 4083 (1994); S. Kobayashi, M. Araki, and I. Hachiya, J. Org. Chem., 59, 3758 (1994); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996), and references cited therein.
42. S. Kobayashi and H. Ishitani, J. Am. Chem. Soc., 116, 4083 (1994); S. Kobayashi, M. Araki, and I. Hachiya, J. Org. Chem., 59, 3758 (1994); H. Ishitani and S. Kobayashi, Tetrahedron Lett., 37, 7357 (1996), and references cited therein.
43. We have found that reverse enantioselectivity was observed when a chiral scandium catalyst was used in stead of the chiral ytterbium catalyst (the same chiral source). Further investigations are under way and will be reported in due course.
44. This work was partially supported by a grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan. H.I. thanks the JSPS fellowship for Japanese Junior Scientists.