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Allylic azide rearrangement in tandem with Huisgen cycloaddition for stereoselective annulation: synthesis of C-Glycosyl iminosugars

Moynihan, Lorna
; 
Chadda, Rekha
; 
McArdle, Patrick
; 
Murphy, Paul V.
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Identifiers
http://hdl.handle.net/10379/5941
 https://doi.org/10.13025/15060
Publication Date
2015-12-09
Keywords
Chemistry, Inhibition, Transformations, Mechanism
Type
Article
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Citation
Moynihan, Lorna, Chadda, Rekha, McArdle, Patrick, & Murphy, Paul V. (2015). Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars. Organic Letters, 17(24), 6226-6229. doi: 10.1021/acs.orglett.5b03209
Abstract
Allylic azide rearrangement is used. in,tandem with. intramolecular azide-alkene cycloaddition to give a triazoline that when subsequently decomposed in the presence of a nucleophile gives piperidines. The tandem reaction gives two stereocenters that are generated With high control. The formation of-the piperidines required the presence of innate conformational constraint. The-applicability of the annulation reaction is demonstrated by the synthesis iminosugars. A proposal is included to account for the observed stereoselectivity, which is influenced by the precursor structure.
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Publisher
American Chemical Society
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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School of Biological and Chemical Sciences (Scholarly Articles)