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

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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

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Article information


Submitted
24 Apr 2020
Accepted
02 Jun 2020
First published
02 Jun 2020

This article is Open Access

Chem. Commun., 2020, Advance Article
Article type
Communication

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, Advance Article , DOI: 10.1039/D0CC02976A

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