Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR
Identifieur interne : 000D67 ( Main/Exploration ); précédent : 000D66; suivant : 000D68Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR
Auteurs : Erwan Galardon [France] ; Paul Le Maux [France] ; Arnaud Bondon [France] ; Gérard Simonneaux [France]Source :
- Tetrahedron: Asymmetry [ 0957-4166 ] ; 1999.
Abstract
The synthesis of a (carbonyl) (valine methyl ester) ruthenium(II) picket-fence complex bearing optically active α-methoxy-α(trifluoromethyl)phenylacetyl residues on both sides of the porphyrin plane (α,β,α,β-isomer) is described. For various amino esters, chiral recognition was observed for the complexation of the ligand with up to 52% enantiomeric excess for tert-leucine methyl ester. The dissociation rate constants of the two enantiomers of valine methyl ester were determined by 1H NMR using magnetization transfer experiments, showing that the origin of the enantioselectivity in favour of the (l)-valine (ca. 2.6:1) resides in the difference between the kinetics of the axial ligand dissociation of the two enantiomers.
Url:
DOI: 10.1016/S0957-4166(99)00448-6
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 000F88
- to stream Istex, to step Curation: 000B25
- to stream Istex, to step Checkpoint: 000663
- to stream Main, to step Merge: 000D95
- to stream Main, to step Curation: 000D67
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title>Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR</title><author><name sortKey="Galardon, Erwan" sort="Galardon, Erwan" uniqKey="Galardon E" first="Erwan" last="Galardon">Erwan Galardon</name></author><author><name sortKey="Le Maux, Paul" sort="Le Maux, Paul" uniqKey="Le Maux P" first="Paul" last="Le Maux">Paul Le Maux</name></author><author><name sortKey="Bondon, Arnaud" sort="Bondon, Arnaud" uniqKey="Bondon A" first="Arnaud" last="Bondon">Arnaud Bondon</name></author><author><name sortKey="Simonneaux, Gerard" sort="Simonneaux, Gerard" uniqKey="Simonneaux G" first="Gérard" last="Simonneaux">Gérard Simonneaux</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:5734F2202AFE0C9F47F6E3210B3D98EC88EDB386</idno><date when="1999" year="1999">1999</date><idno type="doi">10.1016/S0957-4166(99)00448-6</idno><idno type="url">https://api.istex.fr/document/5734F2202AFE0C9F47F6E3210B3D98EC88EDB386/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">000F88</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">000F88</idno><idno type="wicri:Area/Istex/Curation">000B25</idno><idno type="wicri:Area/Istex/Checkpoint">000663</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000663</idno><idno type="wicri:doubleKey">0957-4166:1999:Galardon E:chiral:recognition:of</idno><idno type="wicri:Area/Main/Merge">000D95</idno><idno type="wicri:Area/Main/Curation">000D67</idno><idno type="wicri:Area/Main/Exploration">000D67</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a">Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR</title><author><name sortKey="Galardon, Erwan" sort="Galardon, Erwan" uniqKey="Galardon E" first="Erwan" last="Galardon">Erwan Galardon</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Bretagne</region><settlement type="city">Rennes</settlement></placeName><orgName type="university">Université de Rennes 1</orgName></affiliation></author><author><name sortKey="Le Maux, Paul" sort="Le Maux, Paul" uniqKey="Le Maux P" first="Paul" last="Le Maux">Paul Le Maux</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Bretagne</region><settlement type="city">Rennes</settlement></placeName><orgName type="university">Université de Rennes 1</orgName></affiliation></author><author><name sortKey="Bondon, Arnaud" sort="Bondon, Arnaud" uniqKey="Bondon A" first="Arnaud" last="Bondon">Arnaud Bondon</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Bretagne</region><settlement type="city">Rennes</settlement></placeName><orgName type="university">Université de Rennes 1</orgName></affiliation></author><author><name sortKey="Simonneaux, Gerard" sort="Simonneaux, Gerard" uniqKey="Simonneaux G" first="Gérard" last="Simonneaux">Gérard Simonneaux</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Bretagne</region><settlement type="city">Rennes</settlement></placeName><orgName type="university">Université de Rennes 1</orgName></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron: Asymmetry</title><title level="j" type="abbrev">TETASY</title><idno type="ISSN">0957-4166</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1999">1999</date><biblScope unit="volume">10</biblScope><biblScope unit="issue">21</biblScope><biblScope unit="page" from="4203">4203</biblScope><biblScope unit="page" to="4210">4210</biblScope></imprint><idno type="ISSN">0957-4166</idno></series><idno type="istex">5734F2202AFE0C9F47F6E3210B3D98EC88EDB386</idno><idno type="DOI">10.1016/S0957-4166(99)00448-6</idno><idno type="PII">S0957-4166(99)00448-6</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0957-4166</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The synthesis of a (carbonyl) (valine methyl ester) ruthenium(II) picket-fence complex bearing optically active α-methoxy-α(trifluoromethyl)phenylacetyl residues on both sides of the porphyrin plane (α,β,α,β-isomer) is described. For various amino esters, chiral recognition was observed for the complexation of the ligand with up to 52% enantiomeric excess for tert-leucine methyl ester. The dissociation rate constants of the two enantiomers of valine methyl ester were determined by 1H NMR using magnetization transfer experiments, showing that the origin of the enantioselectivity in favour of the (l)-valine (ca. 2.6:1) resides in the difference between the kinetics of the axial ligand dissociation of the two enantiomers.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Région Bretagne</li></region><settlement><li>Rennes</li></settlement><orgName><li>Université de Rennes 1</li></orgName></list><tree><country name="France"><region name="Région Bretagne"><name sortKey="Galardon, Erwan" sort="Galardon, Erwan" uniqKey="Galardon E" first="Erwan" last="Galardon">Erwan Galardon</name></region><name sortKey="Bondon, Arnaud" sort="Bondon, Arnaud" uniqKey="Bondon A" first="Arnaud" last="Bondon">Arnaud Bondon</name><name sortKey="Le Maux, Paul" sort="Le Maux, Paul" uniqKey="Le Maux P" first="Paul" last="Le Maux">Paul Le Maux</name><name sortKey="Simonneaux, Gerard" sort="Simonneaux, Gerard" uniqKey="Simonneaux G" first="Gérard" last="Simonneaux">Gérard Simonneaux</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Terre/explor/CobaltMaghrebV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000D67 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000D67 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Terre
|area= CobaltMaghrebV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= ISTEX:5734F2202AFE0C9F47F6E3210B3D98EC88EDB386
|texte= Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR
}}
| This area was generated with Dilib version V0.6.32. |  |