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Haloacetal Radical Cyclizations of α- and β-Hydroxyhydrazones
Journal article   Peer reviewed

Haloacetal Radical Cyclizations of α- and β-Hydroxyhydrazones

Gregory K Friestad and Gina M Fioroni
Organic letters, Vol.7(12), pp.2393-2396
06/09/2005
DOI: 10.1021/ol050663r
PMID: 15932206

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Abstract

Haloacetal radical cyclizations of α- and β-hydroxyhydrazones provide a direct access to aminosugarlike compounds. Stereocontrol of this process is influenced by stereogenic centers of both the hydroxyhydrazone and the acetal. The outcomes are consistent with chair and twist transition states with the anomeric alkoxy group in pseudoaxial orientations.

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