28031-50-7Relevant academic research and scientific papers
Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
Ramsden, Jeremy I.,Heath, Rachel S.,Derrington, Sasha R.,Montgomery, Sarah L.,Mangas-Sanchez, Juan,Mulholland, Keith R.,Turner, Nicholas J.
, p. 1201 - 1206 (2019/01/21)
The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.
Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing
Montgomery, Sarah L.,Mangas-Sanchez, Juan,Thompson, Matthew P.,Aleku, Godwin A.,Dominguez, Beatriz,Turner, Nicholas J.
supporting information, p. 10491 - 10494 (2017/08/22)
The reductive aminase from Aspergillus oryzae (AspRedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH-150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus (TeSADH W110A)) in a redox-neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee, releasing water as the only byproduct.
Synthesis of secondary amines by reduction of α-amidoalkylphenyl sulfones with sodium acetoxyborohydride
Mataloni, Michela,Petrini, Marino,Profeta, Roberto
, p. 1129 - 1132 (2007/10/03)
α-Amidoalkylphenyl sulfones are stable precursors of reactive N-acylimines and can be fully reduced to the corresponding secondary amines using sodium acetoxyborohydride in dioxane at reflux.
