Efficient conditions for the synthesis of C-glycosylidene derivatives: A direct and stereoselective route to C-glycosyl compounds

Tetrahedron Asymmetry

Volumn 11, Issue 2, 2000, Pages 417-421

  Lakhrissi, Y ^a   Taillefumier, C ^a   Lakhrissi, M ^b   Chapleur, Y ^a  

^a NANCY UNIVERSITÉ   (France)

^b IBN TOFAIL UNIVERSITY   (Morocco)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; LACTONE; LACTONE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; REDUCTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034635618     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00586-8     Document Type: Article

References (38)

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26. (b) Taillefumier, C.; Lakhrissi, M.; Chapleur, Y. Synlett 1999, 697-700.
27. An interesting application of our olefination procedure to aminosugar derived lactones has been reported recently: Molina, A.; Czernecki, S.; Xie, J. Tetrahedron Lett. 1998, 39, 7507-7510. See also Ref. 20.
28. For other approaches to enol ether from lactones see Csuk, R.; Glanzer, B. I. Tetrahedron 1991, 47, 1655-1664. See also Ref. 3i.
29. For other approaches to enol ether from thionolactones, see Lee, H. K.; Kim, J.; Pak, C. S. Tetrahedron Lett. 1999, 40, 6267-6270.
30. Maybe inspired by our work, one example of Wittig olefination of the carbonyl group of oxazolidinone derived from aminoacids in toluene without racemization has been reported: Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 775-776.
31. Schiemenz, G. P.; Engelhard, H. Chem. Ber. 1961, 94, 578-584. Horner Emmons olefination of lactone 2 using cyanomethylene diethyl phosphonate and NaH or potassium t-butoxide, the latter giving best results, yielded 35 to 50% of a E:Z 1:2 mixture of olefins 3. For the use of this reagent in the olefination of valerolactone, see Dugan, A. J.; Adams, M. A.; Brynes, P. J.; Meinwald, J. Tetrahedron Lett. 1978, 4323-4326.
32. Schiemenz, G. P.; Engelhard, H. Chem. Ber. 1961, 94, 578-584. Horner Emmons olefination of lactone 2 using cyanomethylene diethyl phosphonate and NaH or potassium t-butoxide, the latter giving best results, yielded 35 to 50% of a E:Z 1:2 mixture of olefins 3. For the use of this reagent in the olefination of valerolactone, see Dugan, A. J.; Adams, M. A.; Brynes, P. J.; Meinwald, J. Tetrahedron Lett. 1978, 4323-4326.
33. Typical procedures for the Wittig reaction are as follows: (a) Using reflux conditions: to a solution of lactone (1 mmol) in 15 ml toluene was added (cyanomethylene) triphenylphosphorane (1.20 g, 4 mmol). The mixture was heated under reflux for the indicated time, concentrated and purified on silica gel; (b) Under microwave activation: the heterogeneous mixture of the substrate (0.5 mmol) in dry toluene (2.5 ml) was placed in a 10 ml Pyrex bottle. The bottle was then hermetically closed with a teflon screw cap (to prevent evaporation of the solvent) and subjected to microwave irradiation in a commercial microwave oven (operating at 2450 MHz) for 2 min. After this heating, a period of 30 s was allowed for cooling and the process was repeated for another 2 min. After removal of the solvent column chromatography gave pure C-glycosylidene compounds.
34. Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213-1234.
35. While this work was in progress, successful Wittig olefination of some lactones and hydrazides using microwave activation was reported: Sabitha, G.; Reddy, M. M.; Srinivas, D.; Yadov, J. S. Tetrahedron Lett. 1999, 40, 165-166.
36. To a solution of the C-glycosylidene compound (0.5 mmol) in dry MeOH (15 ml) was added 10% palladium on charcoal (80 mg) and the mixture was stirred under hydrogen atmosphere for 16 h at room temperature. The catalyst was filtered off on Celite and the filtrate concentrated. The crude product was purified on silica gel.
37. Bandzouzi, A.; Chapleur, Y. Carbohydr. Res. 1987, 171, 13-24.
38. Xie, J.; Molina, A.; Czernecki, S. J. Carbohydr. Chem. 1999, 18, 481-498.