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

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• 作者：Lorna Moynihan ; Rekha Chadda ; Patrick McArdle ; Paul V. Murphy
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：December 18, 2015
• 年：2015
• 卷：17
• 期：24
• 页码：6226-6229
• 全文大小：365K
• ISSN：1523-7052

文摘

Allylic azide rearrangement is used in tandem with intramolecular azide鈥揳lkene 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.