Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine

Stephen P. Fletcher, Jordi Solà, Dean Holt, Robert A. Brown, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

27 Citations (Scopus)

Abstract

The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a 13C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with 13CH3I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established.

Original languageEnglish
Article number152
Pages (from-to)1304-1309
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume7
DOIs
Publication statusPublished - 20 Sep 2011

Keywords

  • Amino acid
  • Asymmetric synthesis
  • Conformational memory
  • Isotopic label
  • Isotopomer
  • Quaternary stereogenic centre

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