Highly Enantioselective Rh-Catalyzed Alkenylation of Imines: Synthesis of Chiral Allylic Amines via Asymmetric Addition of Potassium Alkenyltrifluoroborates to N-Tosyl Imines

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• 作者：Balraj Gopula ; Chien-Wei Chiang ; Way-Zen Lee ; Ting-Shen Kuo ; Ping-Yu Wu ; Julian P. Henschke ; Hsyueh-Liang Wu
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：January 17, 2014
• 年：2014
• 卷：16
• 期：2
• 页码：632-635
• 全文大小：260K
• ISSN：1523-7052

文摘

For the first time, simple N-tosyl aryl aldimines, prepared from the condensation of tosyl amide and aromatic aldehydes, can be used as substrates in the rhodium catalyzed 1,2-addition reaction using alkenylboron nucleophiles. In the presence of 1.5 mol % of [RhCl(1e)]₂, enantioselective addition of various potassium alkenyltrifluoroborates to aryl aldimines furnished the corresponding chiral allylic amines in 73鈥?6% yield and 72鈥?gt;99.5% ee. Notably, this method efficiently provides the di-, tri-, and tetrasubstituted allylic N-tosyl amines with high asymmetric induction.