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<p>Developing general protocols that control multiple types of selectivity in a single transformation is challenging yet highly desirable for the synthesis of complex molecules. Here we describe a N-heterocyclic carbene–nickel catalyst that enables simultaneous control over chemo-, regio-, <i>E/Z</i>-, diastereo- and enantioselectivity in a dynamic kinetic resolution (DKR) asymmetric aldehyde–alkyne reductive coupling reaction. This method provides a straightforward synthesis of enantioenriched allylic alcohols from easily available substrates, and has broad scope and excellent functional group compatibility. We applied this protocol to the modification of profen-type drugs and the formal synthesis of sphingosine. Control experiments reveal that the stereocontrol is influenced by the rate of racemization. We expect the reported process to further stimulate the development of dynamic kinetic resolution chemistry and simplify the synthesis of valuable complex molecules.</p><p></p>

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Selective dynamic kinetic asymmetric aldehyde–alkyne reductive coupling

  • 期刊论文

  • 发表日期：

    2025年9月19日

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  • Guang Chen,
  • Jia-Ming Liu,
  • Lin-Xin Ruan,
  • Shi-Liang Shi

摘要

Developing general protocols that control multiple types of selectivity in a single transformation is challenging yet highly desirable for the synthesis of complex molecules. Here we describe a N-heterocyclic carbene–nickel catalyst that enables simultaneous control over chemo-, regio-, E/Z-, diastereo- and enantioselectivity in a dynamic kinetic resolution (DKR) asymmetric aldehyde–alkyne reductive coupling reaction. This method provides a straightforward synthesis of enantioenriched allylic alcohols from easily available substrates, and has broad scope and excellent functional group compatibility. We applied this protocol to the modification of profen-type drugs and the formal synthesis of sphingosine. Control experiments reveal that the stereocontrol is influenced by the rate of racemization. We expect the reported process to further stimulate the development of dynamic kinetic resolution chemistry and simplify the synthesis of valuable complex molecules.