Ruthenium and Iron-Catalysed Decarboxylative N-alkylation of Cyclic α-Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives

被引:20
作者
Afanasenko, Anastasiia [1 ]
Hannah, Rachael [1 ]
Yan, Tao [1 ]
Elangovan, Saravanakumar [1 ]
Barta, Katalin [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands
基金
欧洲研究理事会;
关键词
decarboxylation; iron; N-alkylation; N-heterocycles; proline; AZOMETHINE YLIDES; BOND FORMATION; PROLINE; AMINATION; ACTIVATION; COMPLEXES; MECHANISM; PYRIDINE; OXIDE;
D O I
10.1002/cssc.201901499
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A modular and waste-free strategy for constructing N-substituted cyclic amines via decarboxylative N-alkylation of alpha-amino acids employing ruthenium- and iron-based catalysts is presented. The reported method allows the synthesis of a wide range of five- and six-membered N-alkylated heterocycles in moderate-to-excellent yields starting from predominantly proline and a broad range of benzyl alcohols, and primary and secondary aliphatic alcohols. Examples using pipecolic acid for the construction of piperidine derivatives, as well as the one-pot synthesis of alpha-amino nitriles, are also shown.
引用
收藏
页码:3801 / 3807
页数:7
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