Complementary stereoselectivity in the reactions of hexopyranosid-4-uloses with methylmagnesium iodide and methyllithium
โ Scribed by Juji Yoshimura; Ken-Ichi Sato
- Publisher
- Elsevier Science
- Year
- 1983
- Tongue
- English
- Weight
- 289 KB
- Volume
- 123
- Category
- Article
- ISSN
- 0008-6215
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Despite the extensive amount of research on nonenzymatic [1,2]-hydride shifts.2 there have been particularly few reports on similar transfers related to carbohydrates.3 We wish to report here the novel example of the stereoselective [1,2]-hydride shifts which occured in the reactions of methyl 3-0-m
Reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-o-arubino-hex-l-enitol (1; 2hydroxyglucal tetraacetate) with 1.0-1.5 mol of primary, secondary, or tertiary alcohols, in the presence of 0.1-1.0 mol of N-iodosuccinimide (NIS) in acetonitrjle as solvent, afforded the a anomers of alkyl 3-deoxyhex-2-eno