Enantioselective Synthesis of Indole-Annulated Medium-Sized Rings

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• 作者：Lin Huang ; Li-Xin Dai ; Shu-Li You
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：May 11, 2016
• 年：2016
• 卷：138
• 期：18
• 页码：5793-5796
• 全文大小：378K
• 年卷期：0
• ISSN：1520-5126

文摘

Asymmetric synthesis of indole-annulated medium-sized-ring compounds is developed through an iridium-catalyzed allylic dearomatization/retro-Mannich/hydrolysis cascade reaction. The reaction features mild conditions and a broad substrate scope. Under the optimal conditions, various seven-, eight-, or nine-membered-ring compounds can be afforded in good to excellent yields and excellent enantioselectivity. The proposed mechanism is supported by capturing the dearomatized intermediate through in situ reduction.