Mechanistic Insights into the Stereocontrolled Synthesis of Hexahydropyrrolo[2,3-b]indoles by Electrophilic Activation of Tryptophan Derivatives

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• 作者：Carlos Silva Ló ; pez ; Carlos P&eacute ; rez-Balado ; Paula Rodrí ; guez-Grañ ; a ; Á ; ngel R. de Lera
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：January 3, 2008
• 年：2008
• 卷：10
• 期：1
• 页码：77 - 80
• 全文大小：83K
• 年卷期：v.10,no.1(January 3, 2008)
• ISSN：1523-7052

文摘

A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure wasshown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles. Thecorresponding 3a-bromo derivatives have been obtained in high yields and synthetically useful exo/endo ratios.