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<p>Catalytic <i>sp</i><sup>3</sup><i>–sp</i><sup>3</sup> bond-forming reactions have been the subject of considerable interest in both academic and pharmaceutical laboratories. This is largely due to the observation that a higher content of <i>sp</i><sup>3</sup>-hybridized carbons has recently been shown to improve several molecular attributes that contribute to clinical success. Although the ready availability of unactivated olefins and aziridines makes them ideal precursors to forge enantioenriched <i>sp</i><sup>3</sup><i>–sp</i><sup>3</sup> architectures with added-value amine functions, an enantioconvergent catalytic scenario of these counterparts has not yet been realized. Here we describe a nickel-catalysed blueprint that enables the enantioselective construction of amine-containing <i>sp</i><sup>3</sup><i>–sp</i><sup>3</sup> architectures via photoinduced enantioconvergent coupling of racemic aziridines with alkylzirconium reagents generated in situ from unactivated terminal and even internal olefins. The broad applicability of this protocol is illustrated in a series of late-stage diversification of advanced synthetic intermediates.</p><p></p>

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Photoinduced nickel-catalysed enantioconvergent sp3–sp3 coupling of unactivated olefins and aziridines

  • 期刊论文

  • 发表日期：

    2025年3月28日

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  • Liangliang Zhang,
  • Hao Wang,
  • Tomás G. Santiago,
  • Wen-Jun Yue,
  • Ruben Martin

摘要

Catalytic sp3–sp3 bond-forming reactions have been the subject of considerable interest in both academic and pharmaceutical laboratories. This is largely due to the observation that a higher content of sp3-hybridized carbons has recently been shown to improve several molecular attributes that contribute to clinical success. Although the ready availability of unactivated olefins and aziridines makes them ideal precursors to forge enantioenriched sp3–sp3 architectures with added-value amine functions, an enantioconvergent catalytic scenario of these counterparts has not yet been realized. Here we describe a nickel-catalysed blueprint that enables the enantioselective construction of amine-containing sp3–sp3 architectures via photoinduced enantioconvergent coupling of racemic aziridines with alkylzirconium reagents generated in situ from unactivated terminal and even internal olefins. The broad applicability of this protocol is illustrated in a series of late-stage diversification of advanced synthetic intermediates.