Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR
Identifieur interne : 000F88 ( Istex/Corpus ); précédent : 000F87; suivant : 000F89Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR
Auteurs : Erwan Galardon ; Paul Le Maux ; Arnaud Bondon ; Gérard SimonneauxSource :
- 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.
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DOI: 10.1016/S0957-4166(99)00448-6
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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><istex><corpusName>elsevier</corpusName><author><json:item><name>Erwan Galardon</name><affiliations><json:string>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</json:string></affiliations></json:item><json:item><name>Paul Le Maux</name><affiliations><json:string>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</json:string></affiliations></json:item><json:item><name>Arnaud Bondon</name><affiliations><json:string>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</json:string></affiliations></json:item><json:item><name>Gérard Simonneaux</name><affiliations><json:string>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Article</value></json:item></subject><language><json:string>eng</json:string></language><originalGenre><json:string>Full-length article</json:string></originalGenre><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.</abstract><qualityIndicators><score>3.901</score><pdfVersion>1.2</pdfVersion><pdfPageSize>581 x 701 pts</pdfPageSize><refBibsNative>true</refBibsNative><keywordCount>1</keywordCount><abstractCharCount>728</abstractCharCount><pdfWordCount>2689</pdfWordCount><pdfCharCount>14906</pdfCharCount><pdfPageCount>8</pdfPageCount><abstractWordCount>101</abstractWordCount></qualityIndicators><title>Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR</title><pii><json:string>S0957-4166(99)00448-6</json:string></pii><genre><json:string>research-article</json:string></genre><host><volume>10</volume><pii><json:string>S0957-4166(00)X0087-0</json:string></pii><pages><last>4210</last><first>4203</first></pages><issn><json:string>0957-4166</json:string></issn><issue>21</issue><genre><json:string>journal</json:string></genre><language><json:string>unknown</json:string></language><title>Tetrahedron: Asymmetry</title><publicationDate>1999</publicationDate></host><categories><wos><json:string>CHEMISTRY, INORGANIC & NUCLEAR</json:string><json:string>CHEMISTRY, ORGANIC</json:string><json:string>CHEMISTRY, PHYSICAL</json:string></wos></categories><publicationDate>1999</publicationDate><copyrightDate>1999</copyrightDate><doi><json:string>10.1016/S0957-4166(99)00448-6</json:string></doi><id>5734F2202AFE0C9F47F6E3210B3D98EC88EDB386</id><score>0.050213493</score><fulltext><json:item><original>true</original><mimetype>application/pdf</mimetype><extension>pdf</extension><uri>https://api.istex.fr/document/5734F2202AFE0C9F47F6E3210B3D98EC88EDB386/fulltext/pdf</uri></json:item><json:item><original>false</original><mimetype>application/zip</mimetype><extension>zip</extension><uri>https://api.istex.fr/document/5734F2202AFE0C9F47F6E3210B3D98EC88EDB386/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/5734F2202AFE0C9F47F6E3210B3D98EC88EDB386/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a">Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>ELSEVIER</publisher><availability><p>©1999 Elsevier Science Ltd</p></availability><date>1999</date></publicationStmt><notesStmt><note type="content">Fig. 1: Chiral complex</note><note type="content">Scheme. 1:</note><note type="content">Fig. 2:</note><note type="content">Fig. 3: (a) 1H NMR spectrum of 2L; (b) difference spectrum of magnetization transfer experiment with (l)-valine methyl ester. *, irradiated signal; L, ligand excess; ‡, signal corresponding to undesirable magnetization transfer due to partial saturation of the second methyl group of the free ligand</note><note type="content">Fig. 4: (a) 1H NMR spectrum of the racemic mixture (2L+2D) obtained after addition of an excess of racemic valine methyl ester to 1; (b) difference spectrum of magnetization transfer experiment with racemic valine methyl ester</note><note type="content">Table 1: Chiral recognition of amino esters with complex 1</note><note type="content">Table 2: Relaxation time Tobs and dissociation rate constants k of complexes 2L and 2D</note></notesStmt><sourceDesc><biblStruct type="inbook"><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 xml:id="author-1"><persName><forename type="first">Erwan</forename><surname>Galardon</surname></persName><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation></author><author xml:id="author-2"><persName><forename type="first">Paul</forename><surname>Le Maux</surname></persName><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation></author><author xml:id="author-3"><persName><forename type="first">Arnaud</forename><surname>Bondon</surname></persName><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation></author><author xml:id="author-4"><persName><forename type="first">Gérard</forename><surname>Simonneaux</surname></persName><note type="correspondence"><p>Corresponding author. Fax: 02 99 28 16 46; e-mail: simonnea@univ-rennes1.fr</p></note><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation></author></analytic><monogr><title level="j">Tetrahedron: Asymmetry</title><title level="j" type="abbrev">TETASY</title><idno type="pISSN">0957-4166</idno><idno type="PII">S0957-4166(00)X0087-0</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="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></monogr><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></fileDesc><profileDesc><creation><date>1999</date></creation><langUsage><language ident="en">en</language></langUsage><abstract xml:lang="en"><p>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.</p></abstract><textClass><keywords scheme="keyword"><list><head>article-category</head><item><term>Article</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="1999">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><original>false</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/5734F2202AFE0C9F47F6E3210B3D98EC88EDB386/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Elsevier, elements deleted: ce:floats; body; tail"><istex:xmlDeclaration>version="1.0" encoding="utf-8"</istex:xmlDeclaration><istex:docType PUBLIC="-//ES//DTD journal article DTD version 4.5.2//EN//XML" URI="art452.dtd" name="istex:docType"><istex:entity SYSTEM="gr1" NDATA="IMAGE" name="gr1"></istex:entity><istex:entity SYSTEM="sc1" NDATA="IMAGE" name="sc1"></istex:entity><istex:entity SYSTEM="fx2" NDATA="IMAGE" name="fx2"></istex:entity><istex:entity SYSTEM="gr2" NDATA="IMAGE" name="gr2"></istex:entity><istex:entity SYSTEM="gr3" NDATA="IMAGE" name="gr3"></istex:entity><istex:entity SYSTEM="fx3" NDATA="IMAGE" name="fx3"></istex:entity><istex:entity SYSTEM="gr4" NDATA="IMAGE" name="gr4"></istex:entity></istex:docType><istex:document><converted-article version="4.5.2" docsubtype="fla"><item-info><jid>TETASY</jid><aid>3086</aid><ce:pii>S0957-4166(99)00448-6</ce:pii><ce:doi>10.1016/S0957-4166(99)00448-6</ce:doi><ce:copyright year="1999" type="full-transfer">Elsevier Science Ltd</ce:copyright><ce:doctopics><ce:doctopic><ce:text>Article</ce:text></ce:doctopic></ce:doctopics></item-info><head><ce:title>Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by <ce:sup>1</ce:sup>H NMR</ce:title><ce:author-group><ce:author><ce:given-name>Erwan</ce:given-name><ce:surname>Galardon</ce:surname></ce:author><ce:author><ce:given-name>Paul</ce:given-name><ce:surname>Le Maux</ce:surname></ce:author><ce:author><ce:given-name>Arnaud</ce:given-name><ce:surname>Bondon</ce:surname></ce:author><ce:author><ce:given-name>Gérard</ce:given-name><ce:surname>Simonneaux</ce:surname><ce:cross-ref refid="CORR1">*</ce:cross-ref></ce:author><ce:affiliation><ce:textfn>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</ce:textfn></ce:affiliation><ce:correspondence id="CORR1"><ce:label>*</ce:label><ce:text>Corresponding author. Fax: 02 99 28 16 46; e-mail: simonnea@univ-rennes1.fr</ce:text></ce:correspondence></ce:author-group><ce:date-received day="22" month="9" year="1999"></ce:date-received><ce:date-accepted day="7" month="10" year="1999"></ce:date-accepted><ce:abstract><ce:section-title>Abstract</ce:section-title><ce:abstract-sec><ce:simple-para>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 <ce:italic>tert</ce:italic>-leucine methyl ester. The dissociation rate constants of the two enantiomers of valine methyl ester were determined by <ce:sup>1</ce:sup>H NMR using magnetization transfer experiments, showing that the origin of the enantioselectivity in favour of the (<ce:small-caps>l</ce:small-caps>)-valine (ca. 2.6:1) resides in the difference between the kinetics of the axial ligand dissociation of the two enantiomers.</ce:simple-para></ce:abstract-sec></ce:abstract></head></converted-article></istex:document></istex:metadataXml><mods version="3.6"><titleInfo><title>Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by 1H NMR</title></titleInfo><titleInfo type="alternative" contentType="CDATA"><title>Chiral recognition of amino esters by a ruthenium porphyrin complex: kinetics of the exchange process determined by</title></titleInfo><name type="personal"><namePart type="given">Erwan</namePart><namePart type="family">Galardon</namePart><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Paul</namePart><namePart type="family">Le Maux</namePart><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Arnaud</namePart><namePart type="family">Bondon</namePart><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Gérard</namePart><namePart type="family">Simonneaux</namePart><affiliation>Laboratoire de Chimie Organométallique et Biologique, UMR 6509, CNRS and Université de Rennes 1, 35042 Rennes cedex, France</affiliation><description>Corresponding author. Fax: 02 99 28 16 46; e-mail: simonnea@univ-rennes1.fr</description><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="research-article" displayLabel="Full-length article"></genre><originInfo><publisher>ELSEVIER</publisher><dateIssued encoding="w3cdtf">1999</dateIssued><copyrightDate encoding="w3cdtf">1999</copyrightDate></originInfo><language><languageTerm type="code" authority="iso639-2b">eng</languageTerm><languageTerm type="code" authority="rfc3066">en</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType></physicalDescription><abstract 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.</abstract><note type="content">Fig. 1: Chiral complex</note><note type="content">Scheme. 1: </note><note type="content">Fig. 2: </note><note type="content">Fig. 3: (a) 1H NMR spectrum of 2L; (b) difference spectrum of magnetization transfer experiment with (l)-valine methyl ester. *, irradiated signal; L, ligand excess; ‡, signal corresponding to undesirable magnetization transfer due to partial saturation of the second methyl group of the free ligand</note><note type="content">Fig. 4: (a) 1H NMR spectrum of the racemic mixture (2L+2D) obtained after addition of an excess of racemic valine methyl ester to 1; (b) difference spectrum of magnetization transfer experiment with racemic valine methyl ester</note><note type="content">Table 1: Chiral recognition of amino esters with complex 1</note><note type="content">Table 2: Relaxation time Tobs and dissociation rate constants k of complexes 2L and 2D</note><subject><genre>article-category</genre><topic>Article</topic></subject><relatedItem type="host"><titleInfo><title>Tetrahedron: Asymmetry</title></titleInfo><titleInfo type="abbreviated"><title>TETASY</title></titleInfo><genre type="journal">journal</genre><originInfo><dateIssued encoding="w3cdtf">19991029</dateIssued></originInfo><identifier type="ISSN">0957-4166</identifier><identifier type="PII">S0957-4166(00)X0087-0</identifier><part><date>19991029</date><detail type="volume"><number>10</number><caption>vol.</caption></detail><detail type="issue"><number>21</number><caption>no.</caption></detail><extent unit="issue pages"><start>A569</start><end>A594</end></extent><extent unit="issue pages"><start>4065</start><end>4260</end></extent><extent unit="pages"><start>4203</start><end>4210</end></extent></part></relatedItem><identifier type="istex">5734F2202AFE0C9F47F6E3210B3D98EC88EDB386</identifier><identifier type="DOI">10.1016/S0957-4166(99)00448-6</identifier><identifier type="PII">S0957-4166(99)00448-6</identifier><accessCondition type="use and reproduction" contentType="copyright">©1999 Elsevier Science Ltd</accessCondition><recordInfo><recordContentSource>ELSEVIER</recordContentSource><recordOrigin>Elsevier Science Ltd, ©1999</recordOrigin></recordInfo></mods></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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