370-09-2Relevant articles and documents
Ruthenium and Iron-Catalysed Decarboxylative N-alkylation of Cyclic Α-Amino Acids with Alcohols: Sustainable Routes to Pyrrolidine and Piperidine Derivatives
Afanasenko, Anastasiia,Hannah, Rachael,Yan, Tao,Elangovan, Saravanakumar,Barta, Katalin
, p. 3801 - 3807 (2019/07/31)
A modular and waste-free strategy for constructing N-substituted cyclic amines via decarboxylative N-alkylation of α-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 α-amino nitriles, are also shown.
Iridium-catalyzed decarboxylative N-alkylation of α-amino acids with primary alcohols
Wu, Jiashou,Jiang, Huajiang,Chen, Dingben,Shen, Jianfen,Zhao, Datong,Xiang, Jing,Zhou, Qizhong
, p. 539 - 542 (2014/03/21)
A new decarboxylative N-alkylation reaction of α-amino acids has been developed. A variety of tertiary amines were obtained in good to excellent yields via the decarboxylative N-alkylation reaction of α-amino acids with primary alcohols catalyzed by a CpIr complex. Georg Thieme Verlag Stuttgart New York.
An efficient synthesis of nitrogen heterocycles by Cp*Ir-catalyzed N-cycloalkylation of primary amines with diols
Fujita, Ken-ichi,Fujii, Takeshi,Komatsubara, Atsuo,Enoki, Youichiro,Yamaguchi, Ryohei
, p. 673 - 682 (2008/09/18)
A new efficient method for the N-cycloalkylation of primary amines with diols catalyzed by a Cp*Ir complex have been developed. A variety of five-, six-, and seven-membered cyclic amines are synthesized in good to excellent yields in environmentally benign and atom economical manner with the formation of only water as a coproduct. A large scale synthesis of N-benzylpiperidine and a two-step asymmetric synthesis of (S)-2-phenylpiperidine using (R)-1-phenylethylamine as a starting primary amine have been also achieved.