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Nucleophilic RhI Catalyzed Selective Isomerization of Terminal Aziridines to Enamides
ChemCatChem ( IF 3.8 ) Pub Date : 2020-05-20 , DOI: 10.1002/cctc.202000597 Yingying Tian 1 , Doris Kunz 1
ChemCatChem ( IF 3.8 ) Pub Date : 2020-05-20 , DOI: 10.1002/cctc.202000597 Yingying Tian 1 , Doris Kunz 1
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The selective isomerization of various terminal N‐Boc protected aziridines to enamides was realized using the highly reactive nucleophilic rhodium catalyst C with the Lewis acid LiNTf2 as co‐catalyst under moderate conditions. The reaction proceeds smoothly with only 1 mol% catalyst loading and excellent yields were achieved. An intermediate containing an enamide with a non‐conjugated terminal C=C double bond was detected during the course of the reaction, which isomerizes to form the thermodynamically favored 2‐amido styrene. Mechanistic insight is gained based on these observations.
中文翻译：
亲核RhI催化末端氮丙啶选择性异构化成酰胺。
使用高反应性亲核铑催化剂C和路易斯酸LiNTf 2作为助催化剂，在中等条件下实现了各种N - Boc末端保护的氮丙啶选择性异构化为酰胺。反应仅以1mol％的催化剂负载而顺利进行，并且获得了优异的产率。在反应过程中检测到一种中间体，该中间体含有一个非共轭末端C = C双键的酰胺，该中间体异构化形成热力学上较受欢迎的2-氨基苯乙烯。基于这些观察结果获得了机械的见解。
更新日期：2020-05-20
中文翻译：
亲核RhI催化末端氮丙啶选择性异构化成酰胺。
使用高反应性亲核铑催化剂C和路易斯酸LiNTf 2作为助催化剂，在中等条件下实现了各种N - Boc末端保护的氮丙啶选择性异构化为酰胺。反应仅以1mol％的催化剂负载而顺利进行，并且获得了优异的产率。在反应过程中检测到一种中间体，该中间体含有一个非共轭末端C = C双键的酰胺，该中间体异构化形成热力学上较受欢迎的2-氨基苯乙烯。基于这些观察结果获得了机械的见解。
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