BioChem - DOS

Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

Journal of the American Chemical Society

Ramsden, Jeremy I.; Heath, Rachel S.; Derrington, Sasha R.; Montgomery, Sarah L.; Mangas-Sanchez, Juan; Mulholland, Keith R.; Turner, Nicholas J.

<P>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 <I>Aspergillus oryzae</I> is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect <I>N</I>-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.</P><BR>[FIG OMISSION]</BR>

2019

American Chemical Society

0002-7863

1520-5126

141

3

pp.1201-1206

10.1021/jacs.8b11561

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