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

作者：Moynihan Lorna; Chadda Rekha; McArdle Patrick; Murphy Paul V^*

来源：Organic Letters, 2015, 17(24): 6226-6229.

DOI：10.1021/acs.orglett.5b03209

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.

• 出版日期2015-12-18