Chemoenzymatic Dynamic Kinetic Resolution of Amines in Fully Continuous-Flow Mode

Org Lett. 2018 Dec 21;20(24):8052-8056. doi: 10.1021/acs.orglett.8b03676. Epub 2018 Dec 13.

Abstract

In this study, lipase-mediated dynamic kinetic resolution (DKR) of various benzylic amines (1a-g) is presented which is realized in a so far unprecedented fully continuous-flow system. The DKR process applying sol-gel immobilized lipase B from Candida antarctica as biocatalyst, palladium on 3-aminopropyl-functionalized silica as racemization catalyst, isopropyl 2-ethoxyacetate as acylating agent, ammonium formate as hydrogen and nitrogen sources, and 2-methyl-2-butanol as solvent under regulated pressure provided the desired products in moderate to good yields with excellent enantiomeric excesses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Kinetics
  • Molecular Structure
  • Thermodynamics*

Substances

  • Amines