72219-09-1Relevant 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.
Redox-neutral α-cyanation of amines
Ma, Longle,Chen, Weijie,Seidel, Daniel
supporting information, p. 15305 - 15308 (2012/10/29)
α-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine α-cyanation/N-alkylation or alternatively, α-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.
The decarboxylative strecker reaction
Das, Deepankar,Richers, Matthew T.,Ma, Longle,Seidel, Daniel
scheme or table, p. 6584 - 6587 (2012/01/19)
α-Amino acids react with aldehydes in the presence of a cyanide source to form α-amino nitriles in what can be considered a decarboxylative variant of the classical Strecker reaction. This unprecedented transformation does not require the use of a metal catalyst and provides facile access to valuable α-amino nitriles that are inaccessible by traditional Strecker chemistry.
Synthesis of α-CN and α-CF3 N-heterocycles through tandem nucleophilic additions
Han, Junbin,Xu, Bo,Hammond, Gerald B.
supporting information; experimental part, p. 3450 - 3453 (2011/08/07)
Using a readily available secondary aminoalkyne as starting material, a powerful strategy was discovered to prepare precursors of biologically important unnatural cyclic aminoacids and fluorinated N-heterocycles with important ring sizes (e.g., 5-7) in a
Cyclization via carbolithiation of α-amino alkyllithium reagents
Bahde, Robert J.,Rychnovsky, Scott D.
supporting information; experimental part, p. 4017 - 4020 (2009/06/18)
(Chemical Equation Presented) We report a new route to tertiary α-amino stereocenters by sequential alkylation of α-amino nitriles followed by reductive lithiation of the nitrile and cycllzation onto an alkene. Reductive lithiation of α-amino nitriles usi
Acid-catalyzed rearrangement of 1-benzyl-2-methyl-3-piperidone to 1-benzyl-2-acetylpyrrolidine
Zhao, Shengyin,Jeon, Heung-Bae,Nadkarni, Durgesh V.,Sayre, Lawrence M.
, p. 6361 - 6369 (2007/10/03)
We report that 1-benzyl-2-methyl-3-piperidone, conveniently prepared from 3-hydroxy-2-methylpyridine, undergoes rearrangement to 1-benzyl-2-acetylpyrrolidine in aqueous 6 N HCl at reflux. Studies showing that the 2,2-dimethyl analog is inert under the same conditions support a mechanism of reversible tautomeric equilibria via ring-opened intermediates, one of which was independently synthesized and shown to be a kinetically competent intermediate to product.
Trapping of Metabolically Generated Electrophilic Species with Cyanide Ion: Metabolism of 1-Benzylpyrrolidine
Ho, Bert,Castagnoli, Neal
, p. 133 - 139 (2007/10/02)
Incubations of 1-benzylpyrrolidine (4) and specifically deuterium-labeled analogues of 4 with rabbit liver microsomal preparations in the presence of cyanide ion have led to the characterization of 1-benzyl-2-cyanopyrrolidine (13), cis- and trans-1-benzyl
