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Citation: Wang Kefeng, Zhuang Zixi, Ti Huihui, Wu Peishan, Zhao Xin, Wang Honggen. Et2Zn-promoted β-trans-selective hydroboration of ynamide[J]. Chinese Chemical Letters, ;2020, 31(6): 1564-1567. doi: 10.1016/j.cclet.2019.11.008 shu

Et2Zn-promoted β-trans-selective hydroboration of ynamide

  • a.

    Key Laboratory of Molecular Target & Clinical Pharmacology, State Key Laboratory of Respiratory Disease, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital, Guangzhou Medical University, Guangzhou 511436, China

  • b.

    Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

  • c.

    Guangdong Institute of Analysis(China National Analytical Center, Guangzhou), Guangzhou 510070, China

    * Corresponding authors.
    E-mail addresses: tihuihui@126.com (H. Ti), 13500032980@139.com (P. Wu), wanghg3@mail.sysu.edu.cn (H. Wang).
    1 These authors contributed equally to this work.
  • Received Date: 7 October 2019
    Revised Date: 23 October 2019
    Accepted Date: 6 November 2019
    Available Online: 13 November 2019

Figures(4)

  • The trans-hydroboration of alkyne represents a challenging task in organic synthesis. Reported herein is an Et2Zn promoted β-trans hydroboration of ynamides by using N-heterocyclic carbene (NHC)-ligated borane as boryl source. The reaction leads to a stereoselective construction of enamides bearing a valuable boryl substituent. Both aromatic and aliphatic ynamides were applicable to the reaction. Synthetic transformation of the C—B bond in the product via Suzuki-Miyaura coupling provides a simple and stereospecific route to multi-substituted enamides. Mechanistic studies were conducted and the possible mechanism was discussed
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