Issue 57, 2020

Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

Abstract

Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected L-ornithinol and L-lysinol to L-3-N-Cbz-aminopiperidine and L-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.

Graphical abstract: Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

Supplementary files

Article information

Article type
Communication
Submitted
24 Apr 2020
Accepted
02 Jun 2020
First published
02 Jun 2020
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2020,56, 7949-7952

Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades

G. J. Ford, N. Kress, A. P. Mattey, L. J. Hepworth, C. R. Baldwin, J. R. Marshall, L. S. Seibt, M. Huang, W. R. Birmingham, N. J. Turner and S. L. Flitsch, Chem. Commun., 2020, 56, 7949 DOI: 10.1039/D0CC02976A

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