Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades†
Grayson J. Ford,Nico Kress,Ashley P. Mattey,Lorna J. Hepworth,Christopher R. Baldwin,James R. Marshall,Lisa S. Seibt,Min Huang,William R. Birmingham,Nicholas J. Turner,Sabine L. Flitsch
Chemical Communications Pub Date : 06/02/2020 00:00:00 , DOI:10.1039/D0CC02976A
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