Titanium (IV) promoted rearrangement of 6-deoxy-hex-5-enopyranosides into cyclohexanones

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3471-3472

  Sollogoub, Matthieu ^a   Mallet, Jean Maurice ^a   Sinaÿ, Pierre ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; PYRANOSIDE; TITANIUM;

ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032555005     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00529-2     Document Type: Article

References (15)

1. Das, S. K.; Mallet, J.-M.; Sinaÿ, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 493-496.
2. For a review on the conversion of carbohydrate derivatives into substituted cyclohexanes, see : Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831.
3. Ferrier, R. J. J. Chem. Soc., Perkin Trans. 1 1979, 1455-1458.
4. Menicagli, R.; Malanga, C.; Lardicci, L. J. Org. Chem. 1982, 47, 2288-2291;
5. Menicagli, R.; Malanga, C.; Guidi, M.; Lardicci, L. Tetrahedron 1987, 43, 171-177;
6. Menicagli, R.; Malanga, C.; Dell'Innocenti, M.; Lardicci, L. J. Org. Chem. 1987, 52, 5700-5704;
7. Petasis, N. A.; Lu, S. P. J. Am. Chem. Soc. 1995, 117, 6394-6395;
8. Petasis, N. A.; Lu, S. P. Tetrahedron Lett. 1996, 37, 141-144.
9. Koto, S.; Morishima, N.; Kawahara, R.; Ishikawa, K.; Zen, S. Bull. Chem. Soc. Jpn. 1982, 55, 1092-1096.
10. Mukaiyama, T.; Takeuchi, K.; Uchiro, H. Chem. Lett. 1997, 625-626.
11. Semeria, D.; Philippe, M.; Delaumeny, J.-M.; Sepulchre, A.-M.; Gero, D. Synthesis 1983, 710-713.
12. 4 (144 μL, 0.5 mmol) in dry dichloromethane (20 mL) under argon at 0°C. The mixture was stirred at room temperature for 2 h before being used in the reaction described below.
13. 5 : C, 75.31; H, 6.77; Found : C, 75.24; H, 6.85.
14. A similar transition state has been proposed in the case of the Pd(II) promoted Ferrier-II rearrangement : Iimori, T.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 1996, 37, 649-652.
15. The new compounds 4 and 6 have been prepared as described in ref. 1 for the corresponding β-glycosides.