Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

Org Biomol Chem. 2011 Dec 7;9(23):8171-7. doi: 10.1039/c1ob06251d. Epub 2011 Oct 4.

Abstract

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphetamine / chemistry*
  • Kinetics
  • Molecular Structure
  • Phenethylamines / chemical synthesis*
  • Phenethylamines / metabolism*
  • Stereoisomerism

Substances

  • Phenethylamines
  • Amphetamine