Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 7, Issue -, Pages 1304-1309Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.7.152
Keywords
amino acid; asymmetric synthesis; conformational memory; isotopic label; isotopomer; quaternary stereogenic centre
Categories
Funding
- Leverhulme Trust
- EPSRC
- Departament d'Innovacio Universitats i Empresa de la Generalitat de Catalunya
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The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a C-13 label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (CH3I)-C-13. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established.
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