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

The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditi...

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Autores principales: Fletcher, Stephen P, Solà, Jordi, Holt, Dean, Brown, Robert A, Clayden, Jonathan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201042/
https://www.ncbi.nlm.nih.gov/pubmed/22043239
http://dx.doi.org/10.3762/bjoc.7.152
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author Fletcher, Stephen P
Solà, Jordi
Holt, Dean
Brown, Robert A
Clayden, Jonathan
author_facet Fletcher, Stephen P
Solà, Jordi
Holt, Dean
Brown, Robert A
Clayden, Jonathan
author_sort Fletcher, Stephen P
collection PubMed
description The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established.
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spelling pubmed-32010422011-10-31 Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine Fletcher, Stephen P Solà, Jordi Holt, Dean Brown, Robert A Clayden, Jonathan Beilstein J Org Chem Full Research Paper The method of Kouklovsky and coworkers for the enantioselective alkylation of cyclic N-naphthoyl derivatives of amino acids was used to introduce a (13)C label into one of the two enantiotopic methyl groups of 2-aminoisobutyric acid (Aib) by retentive alkylation of L-alanine with (13)CH(3)I. Conditions were identified for optimization of yield and enantiomeric purity, and the absolute configuration of the labelled product was established. Beilstein-Institut 2011-09-20 /pmc/articles/PMC3201042/ /pubmed/22043239 http://dx.doi.org/10.3762/bjoc.7.152 Text en Copyright © 2011, Fletcher et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Fletcher, Stephen P
Solà, Jordi
Holt, Dean
Brown, Robert A
Clayden, Jonathan
Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title_full Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title_fullStr Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title_full_unstemmed Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title_short Synthesis of enantiomerically enriched (R)-(13)C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine
title_sort synthesis of enantiomerically enriched (r)-(13)c-labelled 2-aminoisobutyric acid (aib) by conformational memory in the alkylation of a derivative of l-alanine
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3201042/
https://www.ncbi.nlm.nih.gov/pubmed/22043239
http://dx.doi.org/10.3762/bjoc.7.152
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