Regioselective methylation of the secondary carbinol center of prim, sec-diols

Tetrahedron Letters

Volumn 39, Issue 19, 1998, Pages 3007-3010

  Yoshida, Hifumi ^a   Takada, Akinori ^a   Mitsunobu, Oyo ^a  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLPROPANOL; 3 (TERT BUTYLDIPHENYLSILYL) 2 METHYLPROPANOL; GLYCOL; METHANOL; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSFORMATION; METHYLATION; STEREOCHEMISTRY;

EID: 0032492909     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00445-6     Document Type: Article

References (13)

1. 1. See for example, a) Omura, S. "Macrolide Antibiotics," Academic Press: Orlando, Florida, 1984,
2. b) Cane, D. E.; Celmer, W. D.; Westley, J. W. J. Am. Chem. Soc., 1983, 105, 3594-3600.
3. 2. a) Fukumasa, M.; Furuhashi, K.; Umezawa, J.; Takahashi, O.; Hirai, T., Tetrahedron, Lett., 1991, 32, 1059-1062.
4. b) Lundeen, A. J.; Oehlschlager, A. C., J. Organometal. Chem., 1970; 25, 337-344.
5. c) Crotti, P.; Bussolo, V. D.; Favers, L.; Macchia, F.; Pineschi, M., Tetrahedron Lett., 1994, 35, 6537-6540.
6. 3. Miyazawa, M.; Ishibashi, N.; Ohnuma, S.; Miyashita, M., Tetrahedron Lett., 1997, 38, 3419-3422.
7. 4. For a review of cyclic sulfites and cyclic sulfates, see, Lohray, B. B., Synthesis, 1992, 1035-1052.
8. 5. Fleischer, R.; Galle, D.; Braun, M., Liebigs Ann./Recueil, 1997, 1189-1194.
9. 6. a) Szmant, H. H.; Emerson, W., J. Am. Chem. Soc., 1956, 78, 454-458.
10. b) Rebiere, F.; Kagan, H. B., Tetrahedron Lett., 1989, 30, 3659-3662.
11. c) Rebiere, F.; Samuel, O.; Ricard, L.; Kagan, H. B., J. Org. Chem., 1991, 56, 5991-5999.
12. 7. We are grateful to one of the referees for helpful suggestions.
13. 8. The reaction of glucose 1,2-cyclic sulfites with alcohols in the presence of lanthanide (III) triflates, see, Sanders, W. J.; Kissling, L. L., Tetrahedron Lett., 1994, 35, 7335-7338.