Rhodium-Catalyzed Enantioselective Hydroamination of Alkynes with Indolines

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• 作者：Qing-An Chen ; Zhiwei Chen ; Vy M. Dong
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：July 8, 2015
• 年：2015
• 卷：137
• 期：26
• 页码：8392-8395
• 全文大小：429K
• ISSN：1520-5126

文摘

The hydroamination of internal alkynes via tandem rhodium catalysis gives branched N-allylic indolines with high regio- and enantioselectivity. An acid switch provides access to the linear isomer in preference to the branched isomer by an isomerization mechanism. Mechanistic studies suggest formation of an allene intermediate, which undergoes hydroamination to generate allylic amines instead of the enamine or imine products typically observed in alkyne hydroaminations.