Catalytic asymmetric addition reaction of dialkylzinc to nitrone utilizing tartaric acid ester as a chiral auxiliary

Chemistry Letters

Volumn , Issue 1, 1997, Pages 59-60

  Ukaji, Yutaka ^a   Shimizu, Yuuko ^a   Kenmoku, Yuuichi ^a   Ahmed, Alauddin ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039494594     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.59     Document Type: Article

References (23)

1. S. E. Denmark and O. J.-C. Nicaise, J. Chem. Soc., Chem. Commun., 1996, 999.
2. Y. Ukaji, Y. Kenmoku, and K. Inomata, Tetrahedron: Asymmetry, 7, 53 (1996); Y. Ukaji, T. Hatanaka, A. Ahmed, and K. Inomata, Chem. Lett., 1993, 1313.
3. Y. Ukaji, Y. Kenmoku, and K. Inomata, Tetrahedron: Asymmetry, 7, 53 (1996); Y. Ukaji, T. Hatanaka, A. Ahmed, and K. Inomata, Chem. Lett., 1993, 1313.
4. M. Hayashi, K. Ono, H. Hoshimi, and N. Oguni, Tetrahedron, 52, 7817 (1996).
5. 14
6. In these reactions, the corresponding methylated hydroxylamine 3b was scarcely obtained.
7. 2 The stereochemistry of other hydroxylamines was tentatively assigned by comparison of their specific rotations with those of 3b and 3e.
8. The stereochemical course of dialkylzinc in the asymmetric addition to aldehyde was discussed: a) R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 30, 49 (1991);
9. b) H. Kitajima, K. Ito, and T. Katsuki, Chem. Lett., 1996, 343.
10. The possibility of the alkyl group bridging between metals in organozincs was noted; J. Boersma, "Comprehensive Organometallic Chemistry," ed by G. Wilkinson, Pergamon Press, Oxford (1982), Vol. 2, p. 827.
11. At present, the effect of the ester group in 2 can not be clearly explained. The complex B would exist in the aggregated form, whose structure might influence on the enantioselectivities.
12. Asymmetric reactions using tartaric acid esters: a) Katsuki-Sharpless epoxidation; Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987); T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
13. Asymmetric reactions using tartaric acid esters: a) Katsuki-Sharpless epoxidation; Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, and K. B. Sharpless, J. Am. Chem. Soc., 109, 5765 (1987); T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).
14. b) Oxidation of sulfides; P. Pitchen, E. Duñach, M. N. Deshmukh, and H. B. Kagan, J. Am. Chem. Soc., 106, 8188 (1984).
15. c) Ring-opening reaction: Ref. 3.
16. d) Cyanohydrin formation; M. Hayashi, T. Matsuda, and N. Oguni, J. Chem. Soc., Perkin Trans. 1, 1992, 3135.
17. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem Lett., 1993, 1227; Y. Ukaji, M. Nishimura. and T. Fujisawa, Chem Lett., 1992, 61.
18. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem Lett., 1993, 1227; Y. Ukaji, M. Nishimura. and T. Fujisawa, Chem Lett., 1992, 61.
19. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem Lett., 1993, 1227; Y. Ukaji, M. Nishimura. and T. Fujisawa, Chem Lett., 1992, 61.
20. We have developed the asymmetric cycloaddition reactions using tartaric acid esters as chiral auxiliaries; M. Shimizu, Y. Ukaji, and K. Inomata, Chem. Lett., 1996, 455; Y. Ukaji, K. Sada, and K. Inomata, Chem. Lett., 1993, 1847; Y. Ukaji, K. Sada, and K. Inomata, Chem Lett., 1993, 1227; Y. Ukaji, M. Nishimura. and T. Fujisawa, Chem Lett., 1992, 61.
21. "Isoquinolines," ed by G. Grethe, John Wiley & Sons, Inc., New York (1981).
22. G. Uray and W. Lindner, Tetrahedron, 44, 4357 (1988).
23. N. Ikeda, I. Arai, and H. Yamamoto, J. Am. Chem. Soc. 108, 483 (1986).