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

doi:10.3762/bjoc.7.152

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

28 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 language	English
Article number	152
Pages (from-to)	1304-1309
Number of pages	6
Journal	Beilstein Journal of Organic Chemistry
Volume	7
DOIs	https://doi.org/10.3762/bjoc.7.152
Publication status	Published - 20 Sept 2011

Keywords

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

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title = "Synthesis of enantiomerically enriched (R)-13C-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 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.",

keywords = "Amino acid, Asymmetric synthesis, Conformational memory, Isotopic label, Isotopomer, Quaternary stereogenic centre",

author = "Fletcher, {Stephen P.} and Jordi Sol{\`a} and Dean Holt and Brown, {Robert A.} and Jonathan Clayden",

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Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine. / Fletcher, Stephen P.; Solà, Jordi; Holt, Dean et al.
In: Beilstein Journal of Organic Chemistry, Vol. 7, 152, 20.09.2011, p. 1304-1309.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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T1 - Synthesis of enantiomerically enriched (R)-13C-labelled 2-aminoisobutyric acid (Aib) by conformational memory in the alkylation of a derivative of L-alanine

AU - Fletcher, Stephen P.

AU - Solà, Jordi

AU - Holt, Dean

AU - Brown, Robert A.

AU - Clayden, Jonathan

PY - 2011/9/20

Y1 - 2011/9/20

N2 - 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.

AB - 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.

KW - Amino acid

KW - Asymmetric synthesis

KW - Conformational memory

KW - Isotopic label

KW - Isotopomer

KW - Quaternary stereogenic centre

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DO - 10.3762/bjoc.7.152

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SN - 1860-5397

VL - 7

SP - 1304

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

M1 - 152

ER -

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

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Keywords

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