Sequential SmI2-promoted one- and two-electron reactions of carbohydrates
β Scribed by Eric J. Enholm; Antigone Trivellas
- Book ID
- 103409205
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 163 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Tetrasubstituted furans are obtained in a one-pot, two-step sequence comprising SmI 2 -promoted reduction of a readily available 4,5-epoxyalk-2-ynyl ester followed by Pd(0)-promoted cyclization of the resulting 2,3,4-trien-1-ol in the presence of an aryl halide or triflate.
The effect of substituents on the reactivity and stereoselectivity of the SmI 2 /Pd(0)-promoted ring-contraction of 5-alkynylpyranosides has been examined using substrates substituted only at selected positions. While formation of 2-ethynylcyclopentanols takes place efficiently, an internal alkyne d
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