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Palladium-catalyzed asymmetric allylic C-H alkylation of 1,4-dienes and glycine Schiff bases

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Abstract

A highly regio- and enantioselective allylic C-H alkylation of 1,4-dienes with glycine Schiff bases has been established by chiral palladium-phosphoramidite catalysis. This reaction can proceed under mild conditions and tolerate a wide scope of 1,4-dienes, delivering structurally diverse chiral β-branched a-amino acid surrogates in moderate to high yields and with high levels of regio-, Z/E-, diastereo- and enantioselectivities.

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Acknowledgements

This work was supported by Ministry of Science and Technology of China (2015CB856600), the National Natural Science Foundation of China (21672197, 21602214) and the Chinese Academy of Sciences (XDB20020000).

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Authors and Affiliations

  1. Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

    Tian-Ci Wang, Pu-Sheng Wang & Liu-Zhu Gong

  2. Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences, Hefei, 230026, China

    Liu-Zhu Gong

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  1. Tian-Ci Wang
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  2. Pu-Sheng Wang
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Correspondence to Pu-Sheng Wang or Liu-Zhu Gong.

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Wang, TC., Wang, PS. & Gong, LZ. Palladium-catalyzed asymmetric allylic C-H alkylation of 1,4-dienes and glycine Schiff bases. Sci. China Chem. 63, 454–459 (2020). https://doi.org/10.1007/s11426-019-9687-1

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