Synthesis of Novel Hexahydroindoles from the Dearomatization of Indoline

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• 作者：Brianna L. MacLeod ; Jared A. Pienkos ; Katy B. Wilson ; Michal Sabat ; William H. Myers ; W. Dean Harman
• 刊名：Organometallics
• 出版年：2016
• 出版时间：February 8, 2016
• 年：2016
• 卷：35
• 期：3
• 页码：370-387
• 全文大小：682K
• ISSN：1520-6041

文摘

The transiently stable indoline complex TpW(NO)(PMe₃)(η²-N-ethyl-6,7-indoline) is shown to be a synthon for a broad range of novel hexahydroindoles. The tungsten dearomatizes the indoline, allowing for its sequential protonation, electrophilic addition (e.g., protonation, fluorination, hydroxylation, acylation), nucleophilic addition (e.g., amination, arylation, etheration, alkylation), and reduction, all with well-defined and predictable stereochemistry. The tungsten stereocenter directly governs the stereoselective formation of four adjacent asymmetric carbons originating from the aromatic ring of the indoline.