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Regio- and stereoselective ring opening of 2,3-epoxyalcohols with diethylaluminium azide

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

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
219 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

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 bulky substituents at C-3. The method has been successfully applied also to the synthesis of diaminodiol dipeptide isosteres.

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Ring-opening of epoxyalcohols by diethyl
Ring-opening of epoxyalcohols by diethylaluminium cyanide. Regio- and stereoselective synthesis of 1-cyano-2,3-diols
โœ Fabio Benedetti; Federico Berti; Stefano Norbedo ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 211 KB

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.

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## Abstract For Abstract see ChemInform Abstract in Full Text.