Chemo- and Regioselectivity-Tunable Pd-Catalyzed Allylic Alkylation of Imines

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- a...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2011-09, Vol.133 (36), p.14180-14183
Main Authors: Chen, Jian-Ping, Peng, Qian, Lei, Bai-Lin, Hou, Xue-Long, Wu, Yun-Dong
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Imines - chemistry
Palladium - chemistry
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja2039503