Asymmetric 1,3-dipolar cycloaddition of nitrile oxides to γ-substituted allylic alcohols

Chemistry Letters

Volumn , Issue 10, 1998, Pages 1023-1024

  Yoshida, Yayoi ^a   Ukaji, Yutaka ^a   Fujinami, Shuhei ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000705574     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1023     Document Type: Article

References (16)

1. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
2. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
3. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
4. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
5. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
6. Recently enantioselective 1,3-dipolar cycloadditions of nitrones and trimethylsilyldiazomethane were reported: K. V. Gothelf and K. A. Jørgensen, Acta Chem. Scand., 50, 652 (1996); A. I. Sanchez-Blanco, K. V. Gothelf, and K. A. Jørgensen, Tetrahedron Lett., 38, 7923 (1997); K. Hori, H. Kodama, T. Ohta, and I. Furukawa, Tetrahedron Lett., 37, 5947 (1996); S. Kobayashi, R. Akiyama, M. Kawamura, and H. Ishitani, Chem. Lett., 1997, 1039; S. Kanemasa and Y. Oderaotoshi, J. Synth. Org. Chem. Jpn., 56, 368 (1998); J.-P. G. Seerden, M. M. M. Kuypers, and H. W. Scheeren, Tetrahedron: Asymmetry, 6, 1441 (1995).
7. D. P. Curran and T. A. Heffner, J. Org. Chem., 55, 4585 (1990).
8. Diastereo-and regioselective 1,3-dipolar cycloaddition of nitrile oxides coordinated to magnesium to allylic alcohols was reported: a) S. Kanemasa, M. Nishiuchi, A. Kamimura, and K. Hori, J. Am. Chem. Soc., 116, 2324 (1994);
9. b) S. Kanemasa, K. Okuda, H. Yamamoto, and S. Kaga, Tetrahedron Lett., 38, 4095 (1997).
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12. c) Y. Ukaji, K. Taniguchi, K. Sada, and K. Inomata, Chem. Lett., 1997, 547.
13. 3); 5.12 (2a), 9.27 (2c); 5.12 (2b), 9.27 (2d); 5.34 (4a), 9.27 (5a); 6.42 (4b), 9.54 (5b), 5.85 (7); 6.42 (4c), 9.51 (5c); 8.07 (4d), 9.72 (5d); 5.87 (4e), 9.54 (5e).
14. 4a
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16. w = 0.117).