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首页> 外文期刊>Chemistry: A European journal >A General Strategy for the Synthesis of Enantiomerically Pure Azetidines and Aziridines through Nickel-Catalyzed Cross-Coupling
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A General Strategy for the Synthesis of Enantiomerically Pure Azetidines and Aziridines through Nickel-Catalyzed Cross-Coupling

机译：通过镍催化的交叉偶联合成对映体纯的氮杂环丁烷和氮丙啶的一般策略

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摘要

In this communication, we report a straightforward synthesis of enantiomerically pure 2-alkyl azetidines. The protocol is based on a highly regioselective nickel-catalyzed cross-coupling of aliphatic organozinc reagents with an aziridine that features a tethered thiophenyl group. Activation by methylation transforms the sulfide into an excellent leaving group and triggers the formation of the 2-substituted azetidine core structure by cyclization. In addition, we have expanded this concept to the synthesis of enantiomerically pure, terminal alkyl aziridines. Coupling of a TMS-protected aziridine alcohol, followed by acidic work-up to remove the silyl group, provides 1,2-amino alcohol products that are readily cyclized to aziridines. Both of these sequences display excellent functional group tolerance and deliver the desired azetidine and aziridine products in good to excellent yields.
机译：在此通讯中，我们报告了对映体纯的2-烷基氮杂环丁烷的直接合成。该协议基于脂族有机锌试剂与具有拴系噻吩基团的氮丙啶的高度区域选择性镍催化交叉偶联。通过甲基化的活化将硫化物转化为极好的离去基团，并通过环化触发2-取代的氮杂环丁烷核心结构的形成。另外，我们已经将该概念扩展到对映体纯的末端烷基氮丙啶的合成。 TMS保护的氮丙啶醇的偶联，然后进行酸性处理以除去甲硅烷基，可提供易于环化成氮丙啶的1,2-氨基醇产物。这两个序列均显示出优异的官能团耐受性，并以良好或优异的产率提供所需的氮杂环丁烷和氮丙啶产物。

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