Peer-Reviewed Journal Details
Mandatory Fields
Moynihan, L,Chadda, R,McArdle, P,Murphy, PV
2015
December
Organic Letters
Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C-Glycosyl Iminosugars
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INHIBITION MECHANISM
17
6226
6229
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.
10.1021/acs.orglett.5b03209
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