An Efficient Synthetic Approach to Polycyclic 2,5-Dihydropyrroles from α-Silyloxy Ketones

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• 作者：Cristian Draghici ; Qiufeng Huang ; Matthias Brewer
• 刊名：Journal of Organic Chemistry
• 出版年：2009
• 出版时间：November 6, 2009
• 年：2009
• 卷：74
• 期：21
• 页码：8410-8413
• 全文大小：758K
• 年卷期：v.74,no.21(November 6, 2009)
• ISSN：1520-6904

文摘

A three-step sequence to prepare polycyclic 2,5-dihydropyrroles from α-silyloxy ketones is presented. A Lewis acid-mediated ring fragmentation of cyclic γ-silyloxy-β-hydroxy-α-diazo esters provided tethered aldehyde ynoate intermediates which, when treated with amino acid silyl esters, underwent intramolecular azomethine ylide 1,3-dipolar cycloadditions. The 2,5-dihydropyrrole products were formed in good to excellent yield as single diastereomers.