Mechanistic rationale for the NaBH4 reduction of α-keto esters
Identifieur interne : 001124 ( France/Analysis ); précédent : 001123; suivant : 001125Mechanistic rationale for the NaBH4 reduction of α-keto esters
Auteurs : V. Dalla [France] ; J. P. Catteau [France] ; P. Pale [France]Source :
- Tetrahedron Letters [ 0040-4039 ] ; 1999.
Abstract
An intramolecular hydride delivery process largely contributes during the double reduction of α-keto esters into diols by NaBH4. In the case of enolic α-keto esters, the first step of the process, the reduction of the keto group, occured exclusively through an 1,2-hydride addition despite the predominance of the tautomeric enolic form. The clear-cut difference of reaction rate between enolic and non enolic substrate 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the extremely favorable reaction between this solvent and NaBH4.
Url:
DOI: 10.1016/S0040-4039(99)01006-0
Affiliations:
- France
- Alsace (région administrative), Grand Est, Hauts-de-France, Nord-Pas-de-Calais
- Strasbourg, Villeneuve d'Ascq
- Université Strasbourg 1
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Dalla</name><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Chimie Organique et Macromoléculaire, associé au CNRS, Université des Sciences et Technologies, 59655 Villeneuve d'Ascq</wicri:regionArea><placeName><region type="region" nuts="2">Hauts-de-France</region><region type="old region" nuts="2">Nord-Pas-de-Calais</region><settlement type="city">Villeneuve d'Ascq</settlement></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Catteau, J P" sort="Catteau, J P" uniqKey="Catteau J" first="J. P." last="Catteau">J. P. 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Pale</name><affiliation wicri:level="4"><country xml:lang="fr">France</country><wicri:regionArea>Laboratoire de Réactivité et Synthèse Organique, Institut Le Bel, Université Louis Pasteur, 5 rue Blaise Pascal, 67000 Strasbourg</wicri:regionArea><placeName><region type="region" nuts="2">Grand Est</region><region type="old region" nuts="2">Alsace (région administrative)</region><settlement type="city">Strasbourg</settlement></placeName><orgName type="university">Université Strasbourg 1</orgName></affiliation></author></analytic><monogr></monogr><series><title level="j">Tetrahedron Letters</title><title level="j" type="abbrev">TETL</title><idno type="ISSN">0040-4039</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1999">1999</date><biblScope unit="volume">40</biblScope><biblScope unit="issue">28</biblScope><biblScope unit="page" from="5193">5193</biblScope><biblScope unit="page" to="5196">5196</biblScope></imprint><idno type="ISSN">0040-4039</idno></series><idno type="istex">AC1A4AE717076CF723344FAAC6B74874AFC1BDA5</idno><idno type="DOI">10.1016/S0040-4039(99)01006-0</idno><idno type="PII">S0040-4039(99)01006-0</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0040-4039</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">An intramolecular hydride delivery process largely contributes during the double reduction of α-keto esters into diols by NaBH4. In the case of enolic α-keto esters, the first step of the process, the reduction of the keto group, occured exclusively through an 1,2-hydride addition despite the predominance of the tautomeric enolic form. The clear-cut difference of reaction rate between enolic and non enolic substrate 4 for reaction carried out in methanol is interpreted in terms of competitive hydride consumption due to the extremely favorable reaction between this solvent and NaBH4.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Alsace (région administrative)</li><li>Grand Est</li><li>Hauts-de-France</li><li>Nord-Pas-de-Calais</li></region><settlement><li>Strasbourg</li><li>Villeneuve d'Ascq</li></settlement><orgName><li>Université Strasbourg 1</li></orgName></list><tree><country name="France"><region name="Hauts-de-France"><name sortKey="Dalla, V" sort="Dalla, V" uniqKey="Dalla V" first="V." last="Dalla">V. Dalla</name></region><name sortKey="Catteau, J P" sort="Catteau, J P" uniqKey="Catteau J" first="J. P." last="Catteau">J. P. Catteau</name><name sortKey="Pale, P" sort="Pale, P" uniqKey="Pale P" first="P." last="Pale">P. Pale</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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