Highly stereoselective route to aldol products incorporating fluorine containing methyl groups starting from a single D-glucose-derived intermediate

Tetrahedron Asymmetry

Volumn 8, Issue 8, 1997, Pages 1157-1160

  Yamazaki, Takashi ^a   Hiraoka, Shuichi ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; ORGANOFLUORINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030969356     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00120-1     Document Type: Article

References (34)

1. V. P. Kukhar' and V. A. Soloshonok, Fluorine-containing Amino Acids Synthesis and Properties; John Wiley & Sons: New York, 1995; G. Resnati, Tetrahedron, 1993, 42, 9385; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, John Wiley & Sons: New York, 1990.
2. V. P. Kukhar' and V. A. Soloshonok, Fluorine-containing Amino Acids Synthesis and Properties; John Wiley & Sons: New York, 1995; G. Resnati, Tetrahedron, 1993, 42, 9385; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, John Wiley & Sons: New York, 1990.
3. V. P. Kukhar' and V. A. Soloshonok, Fluorine-containing Amino Acids Synthesis and Properties; John Wiley & Sons: New York, 1995; G. Resnati, Tetrahedron, 1993, 42, 9385; J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, John Wiley & Sons: New York, 1990.
4. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199; T. Hanamoto and T. Fuchikami, J. Org. Chem., 1990, 55, 4969; T. Yokozawa, N. Ishikawa and T. Nakai, Chem. Lett., 1987, 1971; T. Yokozawa, M. Yamaguchi, T. Nakai and N. Ishikawa, Nippon Kagakukai Shi, 1985, 2202; T. Yokozawa, N. Ishikawa and T. Nakai, Tetrahedron Lett., 1984, 25, 3987.
5. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199; T. Hanamoto and T. Fuchikami, J. Org. Chem., 1990, 55, 4969; T. Yokozawa, N. Ishikawa and T. Nakai, Chem. Lett., 1987, 1971; T. Yokozawa, M. Yamaguchi, T. Nakai and N. Ishikawa, Nippon Kagakukai Shi, 1985, 2202; T. Yokozawa, N. Ishikawa and T. Nakai, Tetrahedron Lett., 1984, 25, 3987.
6. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199; T. Hanamoto and T. Fuchikami, J. Org. Chem., 1990, 55, 4969; T. Yokozawa, N. Ishikawa and T. Nakai, Chem. Lett., 1987, 1971; T. Yokozawa, M. Yamaguchi, T. Nakai and N. Ishikawa, Nippon Kagakukai Shi, 1985, 2202; T. Yokozawa, N. Ishikawa and T. Nakai, Tetrahedron Lett., 1984, 25, 3987.
7. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199; T. Hanamoto and T. Fuchikami, J. Org. Chem., 1990, 55, 4969; T. Yokozawa, N. Ishikawa and T. Nakai, Chem. Lett., 1987, 1971; T. Yokozawa, M. Yamaguchi, T. Nakai and N. Ishikawa, Nippon Kagakukai Shi, 1985, 2202; T. Yokozawa, N. Ishikawa and T. Nakai, Tetrahedron Lett., 1984, 25, 3987.
8. T. Konno, T. Yamazaki and T. Kitazume, Tetrahedron, 1996, 52, 199; T. Hanamoto and T. Fuchikami, J. Org. Chem., 1990, 55, 4969; T. Yokozawa, N. Ishikawa and T. Nakai, Chem. Lett., 1987, 1971; T. Yokozawa, M. Yamaguchi, T. Nakai and N. Ishikawa, Nippon Kagakukai Shi, 1985, 2202; T. Yokozawa, N. Ishikawa and T. Nakai, Tetrahedron Lett., 1984, 25, 3987.
9. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
10. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
11. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
12. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
13. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
14. H. Yamanaka, T. Takekawa, K. Morita and T. Ishihara, Tetrahedron Lett., 1996, 37, 1829; G.-Q. Shi, X.-H. Huang and F. Hong, J. Chem. Soc., Perkin Trans 1, 1996, 763; K. Iseki, T. Nagai and Y. Kobayashi, Tetrahedron Lett., 1993, 34, 2169; J.-P. Bouillon, C. Maliverney, R. Merényi and H. G. Viehe, J. Chem. Soc. Perkin Trans. 1, 1991, 2147; Q.-Y. Chen and S.-W. Wu, J. Chem. Soc., Chem. Commun., 1989, 705; I. Rico, D. Cantacuzène and C. Wakselman, Tetrahedron Lett., 1981, 22, 3405.
15. M. Hudlicky, Org. React., 1988, 35, 513; C.-L. J. Wang, Org. React., 1985, 34, 31.
16. M. Hudlicky, Org. React., 1988, 35, 513; C.-L. J. Wang, Org. React., 1985, 34, 31.
17. T. Hagiwara and T. Fuchikami, Synlett, 1995, 717; R. Krishnamurti, D. R. Bellew and G. S. K. Prakash, J. Org. Chem., 1991, 56, 984; T. Umemoto and S. Ishihara, Tetrahedron Lett., 1990, 31, 3579; P. G. Gassman and N. J. O'Reilly, J. Org. Chem., 1987, 52, 2481; T. Kitazume and N. Ishikawa, J. Am. Chem. Soc., 1985, 109, 5186.
18. T. Hagiwara and T. Fuchikami, Synlett, 1995, 717; R. Krishnamurti, D. R. Bellew and G. S. K. Prakash, J. Org. Chem., 1991, 56, 984; T. Umemoto and S. Ishihara, Tetrahedron Lett., 1990, 31, 3579; P. G. Gassman and N. J. O'Reilly, J. Org. Chem., 1987, 52, 2481; T. Kitazume and N. Ishikawa, J. Am. Chem. Soc., 1985, 109, 5186.
19. T. Hagiwara and T. Fuchikami, Synlett, 1995, 717; R. Krishnamurti, D. R. Bellew and G. S. K. Prakash, J. Org. Chem., 1991, 56, 984; T. Umemoto and S. Ishihara, Tetrahedron Lett., 1990, 31, 3579; P. G. Gassman and N. J. O'Reilly, J. Org. Chem., 1987, 52, 2481; T. Kitazume and N. Ishikawa, J. Am. Chem. Soc., 1985, 109, 5186.
20. T. Hagiwara and T. Fuchikami, Synlett, 1995, 717; R. Krishnamurti, D. R. Bellew and G. S. K. Prakash, J. Org. Chem., 1991, 56, 984; T. Umemoto and S. Ishihara, Tetrahedron Lett., 1990, 31, 3579; P. G. Gassman and N. J. O'Reilly, J. Org. Chem., 1987, 52, 2481; T. Kitazume and N. Ishikawa, J. Am. Chem. Soc., 1985, 109, 5186.
21. T. Hagiwara and T. Fuchikami, Synlett, 1995, 717; R. Krishnamurti, D. R. Bellew and G. S. K. Prakash, J. Org. Chem., 1991, 56, 984; T. Umemoto and S. Ishihara, Tetrahedron Lett., 1990, 31, 3579; P. G. Gassman and N. J. O'Reilly, J. Org. Chem., 1987, 52, 2481; T. Kitazume and N. Ishikawa, J. Am. Chem. Soc., 1985, 109, 5186.
22. N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume and S. Nakamura, J. Org. Chem., 1995, 60, 4363; K. Mizutani, T. Yamazaki and T. Kitazume, J. Chem. Soc., Chem. Commun., 1995, 51; T. Yamazaki, H. Iwatsubo and T. Kitazume, Tetrahedron: Asym., 1994, 5, 1823.
23. N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume and S. Nakamura, J. Org. Chem., 1995, 60, 4363; K. Mizutani, T. Yamazaki and T. Kitazume, J. Chem. Soc., Chem. Commun., 1995, 51; T. Yamazaki, H. Iwatsubo and T. Kitazume, Tetrahedron: Asym., 1994, 5, 1823.
24. N. Shinohara, J. Haga, T. Yamazaki, T. Kitazume and S. Nakamura, J. Org. Chem., 1995, 60, 4363; K. Mizutani, T. Yamazaki and T. Kitazume, J. Chem. Soc., Chem. Commun., 1995, 51; T. Yamazaki, H. Iwatsubo and T. Kitazume, Tetrahedron: Asym., 1994, 5, 1823.
25. Very recently, the similar type of structure was reported. See the following: T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613; S. Lavaire, R. Plantier-Royon and C. Portella, J. Carbohydr. Chem., 1996, 15, 361; P. Munier, M.-B. Giudicelli, D. Picq and D. Anker, J. Carbohydr. Chem., 1996, 15, 739; U. Wucherpfennig, T. A. Logothetis, U. Eilitz and K. Burger, Tetrahedron, 1996, 52, 131; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137.
26. Very recently, the similar type of structure was reported. See the following: T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613; S. Lavaire, R. Plantier-Royon and C. Portella, J. Carbohydr. Chem., 1996, 15, 361; P. Munier, M.-B. Giudicelli, D. Picq and D. Anker, J. Carbohydr. Chem., 1996, 15, 739; U. Wucherpfennig, T. A. Logothetis, U. Eilitz and K. Burger, Tetrahedron, 1996, 52, 131; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137.
27. Very recently, the similar type of structure was reported. See the following: T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613; S. Lavaire, R. Plantier-Royon and C. Portella, J. Carbohydr. Chem., 1996, 15, 361; P. Munier, M.-B. Giudicelli, D. Picq and D. Anker, J. Carbohydr. Chem., 1996, 15, 739; U. Wucherpfennig, T. A. Logothetis, U. Eilitz and K. Burger, Tetrahedron, 1996, 52, 131; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137.
28. Very recently, the similar type of structure was reported. See the following: T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613; S. Lavaire, R. Plantier-Royon and C. Portella, J. Carbohydr. Chem., 1996, 15, 361; P. Munier, M.-B. Giudicelli, D. Picq and D. Anker, J. Carbohydr. Chem., 1996, 15, 739; U. Wucherpfennig, T. A. Logothetis, U. Eilitz and K. Burger, Tetrahedron, 1996, 52, 131; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137.
29. Very recently, the similar type of structure was reported. See the following: T. F. Herpin, J. S. Houlton, W. B. Motherwell, B. P. Roberts and J.-M. Weibel, Chem. Commun., 1996, 613; S. Lavaire, R. Plantier-Royon and C. Portella, J. Carbohydr. Chem., 1996, 15, 361; P. Munier, M.-B. Giudicelli, D. Picq and D. Anker, J. Carbohydr. Chem., 1996, 15, 739; U. Wucherpfennig, T. A. Logothetis, U. Eilitz and K. Burger, Tetrahedron, 1996, 52, 131; T. Konno, H. Umetani and T. Kitazume, J. Org. Chem., 1997, 62, 137.
30. W. A. Vinson, K. S. Prickett, B. Spahic and P. R. O. de Montellano, J. Org. Chem., 1983, 48, 4661.
31. D. M. Hall, Carbohydr. Res., 1980, 86, 158.
32. S. Hayashi, T. Nakai, N. Ishikawa, D. J. Burton, D. G. Naae and H. S. Kesling, Chem. Lett., 1979, 983.
33. E. J. Buuene, A. J. Huggard and J. C. Tatlow, J. Chem. Soc. C, 1952, 735.
34. F. Tellier and R. Sauvêtre, J. Fluorine Chem., 1993, 62, 183.