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Enaminosucres et sucres halogénoacétyléniques. Communication préliminaire

✍ Scribed by Jean M. J. Tronchet; Bruno Baehler; Alain Bonenfant

Publisher
John Wiley and Sons
Year
1976
Tongue
German
Weight
232 KB
Volume
59
Category
Article
ISSN
0018-019X

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✦ Synopsis

Enamino‐ and Halogenoacetylenic sugars

Traitment of an aldehydosugar (1) with secondary amines gave in an essentially quantitative yield the expected enamines (4–6). Chloro‐ and bromo‐acetylenic sugars (11–14) were obtained in good yields by reacting with lithium methylphenylamide the corresponding gem‐dihalo‐olefinic sugars (7–10), whereas a Z‐gem‐fluoro‐enamine (17) was formed when the difluoro‐olefinic sugar 15 was submitted to the same reaction. The fluoro‐enamine 17 is a useful synthetic intermediate allowing the preparation of several kinds of C‐glycosylic compounds bearing heterocycles like isoxazole, chromone or coumarin.

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