Highly Stereoselective Introduction of Fluorine-Containing Methyl Groups at 2 Position of D-Glucose

Synlett

Volumn 1997, Issue 6, 1997, Pages 669-670

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

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001968204     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3264     Document Type: Article

References (15)

1. a) Houlton, J. S.; Motherwell, W. B.; Ross, B. C.; Tozer, M. J.; Williams, D. J.; Slawin, A. M. Z. Tetrahedron 1993, 49, 8087.
2. b) Herpin, T. F.; Motherwell, W. B.; Tozer, M. J. Tetrahedron: Asym. 1994, 5, 2269.
3. Herpin, T. F.; Houlton, J. S.; Motherwell, W. B.; Roberts, B. P.; Weibel, J. Chem. Commun. 1996, 613.
4. Serafinowski, P. J.; Barnes, C. L. Tetrahedron 1996, 52, 7929.
5. Hayashi, S.; Nakai, T.; Ishikawa, N.; Burton, D. J.; Naae, D. G.; Kesling, H. S. Chem. Lett. 1979, 983.
6. a) Tellier, F.; Sauvêtre, R. Tetrahedron Lett. 1991, 32, 5963.
7. b) Tellier, F.; Sauvêtre, R. J. Fluorine Chem. 1993, 62, 183.
8. Yamazaki, T.; Hiraoka, S.; Kitazume, T. Tetrahedron: Asym. 1997, 8, in press.
9. Vinson, W. A.; Prickett, K. S.; Spahic, B.; Montellano, P. R. J. Org. Chem. 1983, 48, 4661.
10. A similar type of reaction with nonfluorinated material was reported. a) Nakata, M. J. Synth. Org. Chem. Jpn. 1989, 47, 1146.
11. b) K. Krohn, E. Broser and H. Heins Carbohydr. Res. 1987, 164, 59.
12. c) F. W. Lichtenthaler, E. Kaji and S. Weprek. J. Org. Chem. 1985, 50, 3505.
13. d) S. Danishefsky and C. J. Maring J. Am. Chem. Soc. 1985, 107, 1269.
14. Stereochemistry was not determined yet.
15. Calculations were performed by CACheMechanics v. 3.8 (MM), CACheDynamics V. 3.8 (MD), and CACheMOPAC v. 94.10 (MOPAC) implemented in CAChe Worksystem (SONY/Tektronix Corporation). Conformers, obtained from the MD-MM sequence for finding out the possible ring conformations, followed by the rigid search method with rotating the free single bond in 15° increment for all the obtained cyclic structures, were optimized with MM and further with MOPAC (AM1) by the eigenvector following minimization (EF) method with the extra keyword "gnorm = 0.01", final gradient norm being less than 0.01 kcal/Å. The obtained conformers were eventually employed for the vibrational frequency calculation for their confirmation as the stationary points.