Enantio- and diastereoselective synthesis of isoxazolidines by asymmetric 1,3-dipolar cycloaddition of nitrones

Chemistry Letters

Volumn , Issue 6, 1997, Pages 547-548

  Ukaji, Yutaka ^a   Taniguchi, Katsumi ^a   Sada, Kazunori ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031496734     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.547     Document Type: Article

References (20)

1. "Advances in Cycloaddition," ed by D. P. Curran, Jai Press Inc., Greenwich (1988), Vol. 1 and (1990), Vol. 2.
2. Recently asymmetric 1,3-dipolar cycloadditions of nitrones were reported: J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995); K. V. Gothelf, I. Thomsen, and K. A. Jørgensen, J. Am. Chem. Soc., 118, 59 (1996); K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 61, 346 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996).
3. Recently asymmetric 1,3-dipolar cycloadditions of nitrones were reported: J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995); K. V. Gothelf, I. Thomsen, and K. A. Jørgensen, J. Am. Chem. Soc., 118, 59 (1996); K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 61, 346 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996).
4. Recently asymmetric 1,3-dipolar cycloadditions of nitrones were reported: J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995); K. V. Gothelf, I. Thomsen, and K. A. Jørgensen, J. Am. Chem. Soc., 118, 59 (1996); K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 61, 346 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996).
5. Recently asymmetric 1,3-dipolar cycloadditions of nitrones were reported: J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995); K. V. Gothelf, I. Thomsen, and K. A. Jørgensen, J. Am. Chem. Soc., 118, 59 (1996); K. V. Gothelf, R. G. Hazell, and K. A. Jørgensen, J. Org. Chem., 61, 346 (1996); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996).
6. Diastereo- and regioselective 1,3-dipolar cycloadditions of nitrones mediated by metals were reported: a) S. Kanemasa, T. Tsuruoka, and E. Wada, Tetrahedron Lett., 34, 87 (1993);
7. b) S. Kanemasa and T. Tsuruoka, Chem. Lett., 1995, 49;
8. c) O. Tamura, T. Okabe, T. Yamaguchi, K. Gotanda, K. Noe, and M. Sakamoto, Tetrahedron, 51, 107 (1995).
9. Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455.
10. Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455.
11. 15
12. 1H NMR spectra, IR spectra, and elemental analyses or MS spectra.
13. 2 was used.
14. NOE was observed for 4a,b and 5a,b as shown below. Formula Presented
15. (S)-Alcohol 7 was prepared from (S)-malic acid: M. Barth, F. D. Bellamy, P. Renaut, S. Samreth, and F. Schuber, Tetrahedron, 46, 6731 (1990).
16. 25 in MeOH) were as follows: (2R,4S)-8, +106° (c 0.10); (2S,4R)-8, -4° (c 0.80) [derived from (3S,5R)-5a (5% ee)]; (S)-9, -2° (c 0.93) [derived from (3A,5S)-5b (17% ee)].
17. L. W. Boyle, M. J. Peagram, and G. H. Whitham, J. Chem. Soc. (B), 1971, 1728.
18. In the present reaction, the regioisomer was not produced in contrast to the case of the nitrone having benzoyl group even though zinc alkoxide of allyl alcohol was used, probably due to that the formation of orthoester from (t-butylester moiety and allyl alcohol might be impossible; see, T. Tsuruoka and S. Kanemasa, 69th National Meeting of the Chemical Society of Japan, Kyoto, March 1995, Abstr., 2H831 and Ref. 3a.
19. R. Huisgen, H. Hauck, H. Seidl, and M. Burger, Chem. Ber., 102, 1117 (1969).
20. Y. Inouye, J. Hara, and H. Kakisawa, Chem. Lett., 1980, 1407.