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Copper(I)-catalyzed asymmetric 1,6-conjugate allylation

Author

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  • Chang-Yun Shi

    (Shanghai University of Traditional Chinese Medicine
    University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Zhi-Zhou Pan

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Ping Tian

    (Shanghai University of Traditional Chinese Medicine)

  • Liang Yin

    (Shanghai University of Traditional Chinese Medicine
    University of Chinese Academy of Sciences, Chinese Academy of Sciences)

Abstract

Catalytic asymmetric conjugate allylation of unsaturated carbonyl compounds is usually difficult to achieve, as 1,2-addition proceeds dominantly and high asymmetric induction is a challenging task. Herein, we disclose a copper(I)-NHC complex catalyzed asymmetric 1,6-conjugate allylation of 2,2-dimethyl-6-alkenyl-4H-1,3-dioxin-4-ones. The phenolic hydroxyl group in NHC ligands is found to be pivotal to obtain the desired products. Both aryl group and alkyl group at δ-position are well tolerated with the corresponding products generated in moderate to high yields and high enantioselectivity. Moreover, both 2-substituted and 3-substituted allylboronates serve as acceptable allylation reagents. At last, the synthetic utility of the products is demonstrated in several transformations by means of the versatile terminal olefin and dioxinone groups.

Suggested Citation

  • Chang-Yun Shi & Zhi-Zhou Pan & Ping Tian & Liang Yin, 2020. "Copper(I)-catalyzed asymmetric 1,6-conjugate allylation," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-19293-9
    DOI: 10.1038/s41467-020-19293-9
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    Cited by:

    1. Wan Seok Yoon & Won Jun Jang & Woojin Yoon & Hoseop Yun & Jaesook Yun, 2022. "Copper-catalysed asymmetric reductive cross-coupling of prochiral alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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