An NMR method for determination of configuration of β-substituted carboxylic acids

Thomas R. Hoye, Abdel Sattar S. Hamad, Dmitry O. Koltun, Manomi A. Tennakoon

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

The absolute configuration of the stereogenic center at the β-position of a carboxylic acid can be determined via derivatization with chiral benzylic amines [PhCH(Me)NH2 or 1-NpCH(Me)NH2]. Acids of known configuration and with a variety of β-substituents were subjected to derivatization. Analysis of the signs of the chemical shift differences of substituent protons permits determination of the absolute configuration.

Original languageEnglish (US)
Pages (from-to)2289-2293
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number14
DOIs
StatePublished - Apr 1 2000

Bibliographical note

Funding Information:
This work was supported in part by the National Institutes of Health and an Egyptian Ministry of Education Fellowship (to A.-S.S.H.). We thank Drs. Maren Pink and Victor J. Young of the University of Minnesota X-ray Crystallographic Laboratory for determination of the structure of syn- vi .

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

Keywords

  • Carboxylic acids
  • Configuration
  • NMR spectroscopy
  • Stereochemistry

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