Nonracemic α-Fluoro Aldehydes: Asymmetric Synthesis of 4-Deoxy-4-fluoro-D-arabinopyranose

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7546-7547

  Davis, Franklin A ^a   Kasu, Parimala V N ^a   Sundarababu, Gajendran ^a   Qi, Hongyan ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001755016     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9714829     Document Type: Article

References (45)

1. For reviews on biologically active organofluorine compounds see: (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991. (b) Welch, J. T. Tetrahedron 1987, 43, 3123. (c) Biomedical frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, D.C., 1996.
2. For reviews on biologically active organofluorine compounds see: (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991. (b) Welch, J. T. Tetrahedron 1987, 43, 3123. (c) Biomedical frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, D.C., 1996.
3. For reviews on biologically active organofluorine compounds see: (a) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991. (b) Welch, J. T. Tetrahedron 1987, 43, 3123. (c) Biomedical frontiers of Fluorine Chemistry; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; ACS Symposium Series 639; American Chemical Society: Washington, D.C., 1996.
4. For recent reviews on selective fluorination see: (a) Wilkinson, J. A. Chem. Rev. 1992, 92, 505. (b) Mascaretti, O. A. Aldrichim. Acta 1993, 26, 47.
5. For recent reviews on selective fluorination see: (a) Wilkinson, J. A. Chem. Rev. 1992, 92, 505. (b) Mascaretti, O. A. Aldrichim. Acta 1993, 26, 47.
6. For reviews on the synthesis and properties of chiral organofluorine compounds see: Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. See also: Yamazaki, T.; Welch, J. T.; Plummer, J. S.; Gimi, R. H. Tetrahedron Lett. 1991, 32, 4267.
7. For reviews on the synthesis and properties of chiral organofluorine compounds see: Bravo, P.; Resnati, G. Tetrahedron: Asymmetry 1990, 1, 661. See also: Yamazaki, T.; Welch, J. T.; Plummer, J. S.; Gimi, R. H. Tetrahedron Lett. 1991, 32, 4267.
8. For a review of α-fluorocarbonyl compounds see: Rozen, S. Tetrahedron 1985, 41, 1111.
9. Selective Fluorination in Organic and Bioorganic Chemistry; Welch, J. T., Ed.; ACS Symposium Series 456; American Chemical Society: Washington, D.C., 1991.
10. For reviews on fluorinated carbohydrates see: (a) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91. (b) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195. (c) Welch, J. T. Tetrahedron 1987, 43, 3123. (d) Mann, J. Chem. Soc. Rev. 1987, 16, 381. (e) Curd, P. J. J. Carbohydr. Chem. 1985, 4, 451.
11. For reviews on fluorinated carbohydrates see: (a) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91. (b) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195. (c) Welch, J. T. Tetrahedron 1987, 43, 3123. (d) Mann, J. Chem. Soc. Rev. 1987, 16, 381. (e) Curd, P. J. J. Carbohydr. Chem. 1985, 4, 451.
12. For reviews on fluorinated carbohydrates see: (a) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91. (b) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195. (c) Welch, J. T. Tetrahedron 1987, 43, 3123. (d) Mann, J. Chem. Soc. Rev. 1987, 16, 381. (e) Curd, P. J. J. Carbohydr. Chem. 1985, 4, 451.
13. For reviews on fluorinated carbohydrates see: (a) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91. (b) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195. (c) Welch, J. T. Tetrahedron 1987, 43, 3123. (d) Mann, J. Chem. Soc. Rev. 1987, 16, 381. (e) Curd, P. J. J. Carbohydr. Chem. 1985, 4, 451.
14. For reviews on fluorinated carbohydrates see: (a) Tsuchiya, T. Adv. Carbohydr. Chem. Biochem. 1990, 48, 91. (b) Penglis, A. A. E. Adv. Carbohydr. Chem. Biochem. 1981, 38, 195. (c) Welch, J. T. Tetrahedron 1987, 43, 3123. (d) Mann, J. Chem. Soc. Rev. 1987, 16, 381. (e) Curd, P. J. J. Carbohydr. Chem. 1985, 4, 451.
15. (a) Albano, E. L.; Tolman, R. L.; Robins, R. K. Carbohydr. Res. 1971, 19, 63.
16. (b) Butchard, C. G.; Kent, P. W. Tetrahedron 1971, 27, 3457.
17. (c) Wright, J. A.; Fox, J. J. Carbohydr. Res. 1970, 13, 297.
18. (d) Reichman, U.; Watanabe, K. A.; Fox, J. J. Carbohydr. Res. 1975, 42, 233e.
19. (e) Su, T.-S.; Klein, R. S.; Fox, J. J. J. Org. Chem. 1981, 46, 1790.
20. (f) Lundt, K.; Pedersen, C. Mikrochem. Acta Suppl. 1966, 126.
21. (g) Dax, K.; Glänzer, B. I. Carbohydr. Res. 1987, 162, 13.
22. (h) Bols, M.; Lundt, I. Acta Chem. Scand. 1990, 44, 252.
23. Davis, F. A.; Zhou, P.; Murphy, C. K. Tetrahedron Lett. 1993, 34, 3971.
24. Purrington, S. T.; Lazaridis, N. V.; Bumgardner, C. L. Tetrahedron Lett. 1986, 27, 2715.
25. Suga, H.; Schlosser, M. Tetrahedron 1990, 46, 4261.
26. Szarek, W. A.; Hay, G. W.; Perlmutter, M. M. J. Chem. Soc., Chem. Commun. 1982, 1253.
27. Yamazaki, T.; Yamamoto, T.; Kitazume, T. J. Org. Chem. 1989, 54, 83.
28. Patrick, T. B.; Hosseini, S.; Bains, S. Tetrahedron Lett. 1990, 31, 179.
29. Davis, F. A.; Han, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 4730.
30. Davis, F. A.; Qi, H. Tetrahedron Lett. 1996, 37, 4345.
31. D +7.64 (c 3.86, MeOH); 11, oil.
32. Davis, F. A.; Han, W. Tetrahedron Lett. 1992, 33, 1153.
33. This compound gave satisfactory elemental analysis and had spectral properties consistent with its structure.
34. For low yield (4-5%) syntheses of racemic 4 see: Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1988, 53, 1026. Landini, D.; Albanese, D.; Penso, M. Tetrahedron 1992, 48, 4163.
35. For low yield (4-5%) syntheses of racemic 4 see: Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1988, 53, 1026. Landini, D.; Albanese, D.; Penso, M. Tetrahedron 1992, 48, 4163.
36. Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807.
37. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
38. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
39. The possibility that α-methylbenzylamine could cause some epimerization of the fluoroaldehyde cannot be ruled out, and the ee's are probably minimum values.
40. Davis, F. A.; Zhou, P.; Murphy, C. K. Tetrahedron Lett. 1993, 34, 3971.
41. Crispino, G. A.; Jeong, J.-S.; Kolbe, H. C.; Wang, Z.-H.; Xu, W. D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
42. For reviews on Sharpless AD see: Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761. Kolb, H. C.; VanNiewwenhz, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
43. For reviews on Sharpless AD see: Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761. Kolb, H. C.; VanNiewwenhz, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
44. 1H NMR and may be the hemiacetal that forms the aldehyde on acid hydrolysis.
45. Card, P. J.; Reddy, G. S. J. Org. Chem. 1983, 48, 4734.