Catalytic asymmetric 1,3-dipolar cycloaddition of nitrile oxides to an achiral allyl alcohol utilizing diisopropyl tartrate as a chiral auxiliary

Chemistry Letters

Volumn , Issue 6, 1996, Pages 455-456

  Shimizu, Makoto ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030500933     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.455     Document Type: Article

References (19)

1. "Advances in Cycloaddition," ed by D. P. Curran, Jai Press Inc., Greenwich (1988), Vol. 1 and (1990), Vol. 2.
2. K. Mikami and T. Nakai, Kagaku, Zokan, 124, 177 (1995).
3. Recently catalytic 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).
4. Recently catalytic 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).
5. Recently catalytic 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).
6. Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847.
7. Catalytic Katsuki-Sharpless epoxidation of allylic alcohols using tartaric acid esters was reported: Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc, 109, 5765 (1987).
8. Other catalytic reactions using tartaric acid esters: a) M, Hayashi, T. Matsuda, and N. Oguni, J. Chem. Soc., Perkin Trans. 1, 1992, 3135;
9. b) M. Hayashi, K. Ono, H. Hoshimi, and N. Oguni, J. Chem. Soc., Chem. Commun., 1994, 2699.
10. The effect of the addition of THF for the catalytic asymmetric Diels-Alder reaction was reported: D. Sartor, J. Saffrich, G. Helmchen, C. J. Richards, and H. Lambert, Tetrahedron: Asymmetry, 2, 639 (1991).
11. N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1989); N. Iwasawa, Y. Hayashi, H. Sakurai, and K. Narasaka, Chem. Lett., 1989, 1581; K. Mikami and M. Terada, Tetrahedron, 48, 5671 (1992); D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc., 116, 9430 (1994); M. Kitamura, S. Suga, M. Niwa, and R. Noyori, J. Am. Chem. Soc., 117, 4832 (1995) and references cited therein.
12. N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1989); N. Iwasawa, Y. Hayashi, H. Sakurai, and K. Narasaka, Chem. Lett., 1989, 1581; K. Mikami and M. Terada, Tetrahedron, 48, 5671 (1992); D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc., 116, 9430 (1994); M. Kitamura, S. Suga, M. Niwa, and R. Noyori, J. Am. Chem. Soc., 117, 4832 (1995) and references cited therein.
13. N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1989); N. Iwasawa, Y. Hayashi, H. Sakurai, and K. Narasaka, Chem. Lett., 1989, 1581; K. Mikami and M. Terada, Tetrahedron, 48, 5671 (1992); D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc., 116, 9430 (1994); M. Kitamura, S. Suga, M. Niwa, and R. Noyori, J. Am. Chem. Soc., 117, 4832 (1995) and references cited therein.
14. N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1989); N. Iwasawa, Y. Hayashi, H. Sakurai, and K. Narasaka, Chem. Lett., 1989, 1581; K. Mikami and M. Terada, Tetrahedron, 48, 5671 (1992); D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc., 116, 9430 (1994); M. Kitamura, S. Suga, M. Niwa, and R. Noyori, J. Am. Chem. Soc., 117, 4832 (1995) and references cited therein.
15. N. Oguni, Y. Matsuda, and T. Kaneko, J. Am. Chem. Soc., 110, 7877 (1989); N. Iwasawa, Y. Hayashi, H. Sakurai, and K. Narasaka, Chem. Lett., 1989, 1581; K. Mikami and M. Terada, Tetrahedron, 48, 5671 (1992); D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc., 116, 9430 (1994); M. Kitamura, S. Suga, M. Niwa, and R. Noyori, J. Am. Chem. Soc., 117, 4832 (1995) and references cited therein.
16. 2Zn.
17. Recent progresses on asymmetric syntheses of 2-isoxazolines, see: Y. H. Kim, S. H. Kim, and D. H. Park, Tetrahedron Lett., 34, 6063 (1993); M. T. Rispens, E. Keller, B. Lange, R. W. J. Zijlstra, and B. L Feringa, Tetrahedron: Asymmetry, 5, 607 (1994) and references cited in the literature 4.
18. Recent progresses on asymmetric syntheses of 2-isoxazolines, see: Y. H. Kim, S. H. Kim, and D. H. Park, Tetrahedron Lett., 34, 6063 (1993); M. T. Rispens, E. Keller, B. Lange, R. W. J. Zijlstra, and B. L Feringa, Tetrahedron: Asymmetry, 5, 607 (1994) and references cited in the literature 4.
19. Diastereo-and regioselective 1,3-dipolar cycloaddition of nitrile oxide coordinated to metal was reported: S. Kanemasa, M. Nishiuchi, A. Kamimura, and K. Hori, J. Am. Chem. Soc., 116, 2324 (1994).