Palladium-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to olefins

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5947-5950

  Hori, Kazushige ^a   Kodama, Hidehiko ^a   Ohta, Tetsuo ^a   Furukawa, Isao ^a  

^a DOSHISHA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; NITRO DERIVATIVE; PALLADIUM; PHOSPHINE; SESQUITERPENE DERIVATIVE;

ARTICLE; CYCLIZATION; ENANTIOMER; SYNTHESIS;

EID: 0030581362     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01284-1     Document Type: Article

References (29)

1. 1) a) Tufariello, J. J. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; Vol.2, p 83.
2. b) Torssell, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
3. 2) a) Brandi, A.; Cicchi, S.; Goti, A.; Pietrusiewicz, K. M.; Zablocka, M.; Wieniewski, W. J. Org. Chem. 1991, 56, 4383-4388.
4. b) Takahashi, T.; Fujii, A.; Sugita, J.; Hagi, T.; Kitano, K.; Arai, Y.; Koizumi, T. Tetrahedron:Asymmetry 1991, 2, 1379-1390.
5. c) Iyo, M.; Maeda, M.; Kibayashi, C. Tetrahedron Lett. 1992, 33, 3765-3768.
6. d) Bravo, P.; Bruche, L.; Farina, A.; Fronza, G.; Meille, S. V.; Merli, A. Tetrahedron:Asymmetry 1993, 4, 2131-2134.
7. e) Murahashi, S.-I.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395-396.
8. f) Saito, S.; Ishikawa, T.; Moriwake, T. Synlett 1994, 279-281.
9. g) Louis, C.; Hootelé, C. Tetrahedron:Asymmetry 1995, 6, 2149-2152.
10. h) Ina, H.; Ito, M.; Kibayashi, C. J. Org. Chem. 1996, 61, 1023-1029.
11. 3) a) Mukai, C.; Kim, I. J.; Cho, W. J.; Kido, M.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1993, 2495-2503.
12. b) Saito, S.; Ishikawa, T.; Kishimoto, K.; Kohara, T.; Moriwake, T. Synlett 1994, 282 -284.
13. c) Brandi, A.; Cicchi, S.; Goti, A. J. Org. Chem. 1994, 59, 1315-1318.
14. d) van den Broek, L. A. G. M. Tetrahedron 1995, 52, 4467-4478.
15. e) Broggini, G.; Folcio, F.; Sardone, N.; Sonzogni, M.; Zecchi, G. Tetrahedron:Asymmetry 1996, 7, 797-806.
16. 4) a) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5691.
17. b) Gothelf, K. V.; Thomsen, I.; Jørgensen, K. A. J. Am. Chem. Soc. 1996, 118, 59-64.
18. c) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 346-355.
19. 5) a) Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
20. b) Seerden, J.-P. G.; Kuypers, M. M. M; Scheeren, H. W. Tetrahedron:Asymmetry 1995, 6, 1441-1450.
21. 6) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
22. 7) Chan, K. S.; Yeung, M. L.; Chan, W.-K.; Wang, R.-J.; Mak, T. C. W. J. Org. Chem. 1995, 60, 1741 -1747.
23. 8) For the chiral phosphine ligands used and their abbreviations, see: a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
24. b) Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Seyden-Penne, J., Ed.; Wiley: New York, 1995.
25. 1H NMR spectra by coupling constants as well as NOE analysis. a) Coupling constants are shown below: Huisgen, R.; Hauck, H.; Seidl, H.; Burger, M. Chem. Ber., 1969, 102, 1117-1128.
26. -1. (equation presented)
27. R = 24.0 and 28.5 min).
28. 2 (up to 0.12 eq. to 1) in three portions. In the course of this addition, all signals of 1 became broad in NMR spectra and then they returned to the original shape after addition of 2 (1.0 eq. to 1) to the above mixture.
29. 12) Kanemasa, S.; Uemura, T.; Wada, E. Tetrahedron Lett. 1992, 33, 7889-7892.