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Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols

โœ Scribed by Fabio Benedetti; Federico Berti; Stefano Norbedo

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
211 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Diethylaluminium cyanide is a highly selective reagent for the ring opening of 2,3-epoxyalcohols under mild conditions; the reaction takes place at C-3, with inversion of configuration, to give 1-cyano-2,3-diols.

๐Ÿ“œ SIMILAR VOLUMES

Regio- and stereoselective ring opening
Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide
โœ Fabio Benedetti; Federico Berti; Stefano Norbedo ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 219 KB

2,3-Epoxyalcohols react with diethylaluminium azide under mild conditions to give 3-azido-l,2-diols resulting from the regio-and stereoseleetive attack of the nucleophile at the epoxide C-3. The high regioseleetivity (>25:1) observed with both cis and trans substituted epoxides is not affected by bu