American Chemical Society
ol5b03209_si_003.pdf (2.39 MB)

Allylic Azide Rearrangement in Tandem with Huisgen Cycloaddition for Stereoselective Annulation: Synthesis of C‑Glycosyl Iminosugars

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journal contribution
posted on 2015-12-18, 00:00 authored by Lorna Moynihan, Rekha Chadda, Patrick McArdle, Paul V. Murphy
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 of iminosugars. A proposal is included to account for the observed stereoselectivity, which is influenced by the precursor structure.