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

Abstract:
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.
Publication status:
Published

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Publisher copy:
10.3762/bjoc.7.152

Authors


Fletcher, SP More by this author
Clayden, J More by this author
Journal:
Beilstein journal of organic chemistry
Volume:
7
Pages:
1304-1309
Publication date:
2011
DOI:
EISSN:
1860-5397
ISSN:
1860-5397
URN:
uuid:c25ceb9b-9fc4-472d-818c-1774ed1bc6ad
Source identifiers:
179989
Local pid:
pubs:179989

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