Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines
Scandium(III) Triflate Catalyzed Direct Synthesis of N-Unprotected Ketimines
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三氟甲磺酸钪(III)催化直接合成N-未保护的酮亚胺
DOI：
10.1021/acs.orglett.9b04038
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发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Ohshima Takashi
中科院分区：
文献类型：
--
作者：
Kondo Yuta;Kadota Tetsuya;Hirazawa Yoshinobu;Morisaki Kazuhiro;Morimoto Hiroyuki;Ohshima Takashi
N-未保护的酮亚胺是合成有价值的含氮化合物的有用底物和中间体，但其潜在的应用受到现有合成方法的限制。为了解决这个问题，我们报道了一种三氟甲磺酸钪（III）催化的N-未保护的酮亚胺的直接合成。使用市售试剂和刘易斯酸催化剂，酮直接转化为相应的N-未保护的酮亚胺，即使在数克规模下也具有高收率和宽官能团耐受性。该反应适用于一锅法合成甘氨酸席夫碱等重要化合物，无需分离N-未保护的酮亚胺中间体。初步的机理研究，以澄清反应机理也进行了说明。
N-Unprotected ketimines are useful substrates and intermediates for synthesizing valuable nitrogen-containing compounds, but their potential applicability is limited by the available synthetic methods. To address this issue, we report a scandium(III) triflate catalyzed direct synthesis ofN-unprotected ketimines. Using commercially available reagents and Lewis acid catalysts, ketones were directly transformed into the correspondingN-unprotected ketimines in high yields with broad functional group tolerance, even in multigram scales. The reactions were readily applicable for one-pot synthesis of important compounds such as a glycine Schiff base without isolation ofN-unprotected ketimine intermediates. Preliminary mechanistic studies to clarify the reaction mechanism are also described.