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

Autor: Ford GJ; Department of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK. Sabine.flitsch@manchester.ac.uk., Kress N, Mattey AP, Hepworth LJ, Baldwin CR, Marshall JR, Seibt LS, Huang M, Birmingham WR, Turner NJ, Flitsch SL
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2020 Jul 21; Vol. 56 (57), pp. 7949-7952. Date of Electronic Publication: 2020 Jun 12.
DOI: 10.1039/d0cc02976a
Abstrakt: 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.
Databáze: MEDLINE