Highly enantioselective hydrogenation of N-unprotected indoles using (S)-C₁₀-BridgePHOS as the chiral ligand

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• 作者：Chao Li ; Jianzhong Chen ; Guanghong Fu ; Delong Liu ; Yangang Liu ; Wanbin Zhang
• 关键词：(S)-C10&ndash ; BridgePHOS ; Pd-catalyzed enantioselective hydrogenation ; Chiral indoline ; N-Unprotected indole
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：19 August, 2013
• 年：2013
• 卷：69
• 期：33
• 页码：6839-6844
• 全文大小：572 K

文摘

(S)-C₁₀-BridgePHOS was successfully applied to a highly efficient Pd-catalyzed enantioselective hydrogenation of substituted indoles. The methodology was suitable for the hydrogenation of indoles substituted at the 2-, 3- and 2,3-positions. Products were obtained in quantitative conversion and up to 98 % ee. The role the 2-position substituent plays in the hydrogenation process has been proposed. The methodology could be used as an alternative method to synthesize extremely important chiral indolines from N-unprotected indoles.