4.8 Article

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

期刊

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 133, 期 36, 页码 14180-14183

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ja2039503

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资金

  1. Major Basic Research Development Program [2011CB808700]
  2. National Natural Science Foundation of China [20872161, 20821002, 21032007]
  3. CAS [GJHZ200816]
  4. Shanghai Committee of Science and Technology
  5. Croucher Foundation of Hong Kong
  6. Croucher Foundation

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alpha-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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