Chemo- and regioselectivity-tunable Pd-catalyzed allylic alkylation of imines |
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Authors: | Chen Jian-Ping Peng Qian Lei Bai-Lin Hou Xue-Long Wu Yun-Dong |
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Affiliation: | Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China. |
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Abstract: | α-Carbanions of cyclic and acyclic imines have been successfully applied as nucleophiles in the Pd-catalyzed allylic alkylation reaction. Tuning of chemo- and regioselectivity has been realized by using t-BuOK/THF and LDA/toluene to give branched and linear products, respectively, with high regio- and diastereoselectivities. A plausible mechanism is proposed on the basis of the experimental results and DFT calculations. |
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