Assignment of Absolute Configurations for 4-Methylcarnitine Stereoisomers by Proton Nuclear Magnetic Resonance

Academic Article

Abstract

  • We recently reported1 a chromatographic resolution for synthetic precursors of carnitine (5) and 4-methylcarnitine (6), although at that time the absolute configurations of 6 were not assigned. NMR has been increasingly used for such assignments (see ref 2 for a review), and it became apparent that the NMR method of Trost3for determining the absolute configuration of secondary alcohols as their O-methylmandelate esters might be applicable in these systems. Here we report the success of Trost’s model for predicting the known configurations of carnitine enantiomers and describe a simple XH NMR method for establishing the absolute configurations for the two asymmetric centers in the four stereoisomers of 4-methylcarnitine. © 1988, American Chemical Society. All rights reserved.
  • Published In

    Digital Object Identifier (doi)

    Author List

  • Comber RN; Brouillette WJ
  • Start Page

  • 1121
  • End Page

  • 1122
  • Volume

  • 53
  • Issue

  • 5