LeHavreV1, Main, Exploration, bibRecord, 000036

Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.

Identifieur interne : 000036 ( Main/Exploration ); précédent : 000035; suivant : 000037

Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.

Auteurs : Abderrahman El Bouakher [France] ; Ronan Le Goff [France] ; Jordan Tasserie [France] ; Jérôme Lhoste [France] ; Arnaud Martel [France] ; Sébastien Comesse [France]

Source :

Organic letters [ 1523-7052 ] ; 2016.

RBID : pubmed:27128809

Abstract

An original and rapid domino reaction for access to oxazolidin-4-ones is presented. Simply by heating α-bromoamido alcohol in the presence of KNaCO3 and water with readily prepared Michael acceptors, an unprecedented molecular rearrangement is generated. This new methodology enables the hitherto unreported synthesis of functionalized oxazolidin-4-ones. The process was proved to be compatible with a wide variety of substrates, and high regioselectivities were achieved.

DOI: 10.1021/acs.orglett.6b00851
PubMed: 27128809

Affiliations:

Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.</title>
<author><name sortKey="El Bouakher, Abderrahman" sort="El Bouakher, Abderrahman" uniqKey="El Bouakher A" first="Abderrahman" last="El Bouakher">Abderrahman El Bouakher</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Le Goff, Ronan" sort="Le Goff, Ronan" uniqKey="Le Goff R" first="Ronan" last="Le Goff">Ronan Le Goff</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Tasserie, Jordan" sort="Tasserie, Jordan" uniqKey="Tasserie J" first="Jordan" last="Tasserie">Jordan Tasserie</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Lhoste, Jerome" sort="Lhoste, Jerome" uniqKey="Lhoste J" first="Jérôme" last="Lhoste">Jérôme Lhoste</name>
<affiliation wicri:level="3"><nlm:affiliation>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans</wicri:regionArea>
<placeName><region type="region" nuts="2">Pays de la Loire</region>
<settlement type="city">Le Mans</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Martel, Arnaud" sort="Martel, Arnaud" uniqKey="Martel A" first="Arnaud" last="Martel">Arnaud Martel</name>
<affiliation wicri:level="3"><nlm:affiliation>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans</wicri:regionArea>
<placeName><region type="region" nuts="2">Pays de la Loire</region>
<settlement type="city">Le Mans</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2016">2016</date>
<idno type="RBID">pubmed:27128809</idno>
<idno type="pmid">27128809</idno>
<idno type="doi">10.1021/acs.orglett.6b00851</idno>
<idno type="wicri:Area/PubMed/Corpus">000035</idno>
<idno type="wicri:Area/PubMed/Curation">000035</idno>
<idno type="wicri:Area/PubMed/Checkpoint">000035</idno>
<idno type="wicri:Area/Ncbi/Merge">000541</idno>
<idno type="wicri:Area/Ncbi/Curation">000541</idno>
<idno type="wicri:Area/Ncbi/Checkpoint">000541</idno>
<idno type="wicri:Area/Main/Merge">000035</idno>
<idno type="wicri:Area/Main/Curation">000036</idno>
<idno type="wicri:Area/Main/Exploration">000036</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.</title>
<author><name sortKey="El Bouakher, Abderrahman" sort="El Bouakher, Abderrahman" uniqKey="El Bouakher A" first="Abderrahman" last="El Bouakher">Abderrahman El Bouakher</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Le Goff, Ronan" sort="Le Goff, Ronan" uniqKey="Le Goff R" first="Ronan" last="Le Goff">Ronan Le Goff</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Tasserie, Jordan" sort="Tasserie, Jordan" uniqKey="Tasserie J" first="Jordan" last="Tasserie">Jordan Tasserie</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Lhoste, Jerome" sort="Lhoste, Jerome" uniqKey="Lhoste J" first="Jérôme" last="Lhoste">Jérôme Lhoste</name>
<affiliation wicri:level="3"><nlm:affiliation>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans</wicri:regionArea>
<placeName><region type="region" nuts="2">Pays de la Loire</region>
<settlement type="city">Le Mans</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Martel, Arnaud" sort="Martel, Arnaud" uniqKey="Martel A" first="Arnaud" last="Martel">Arnaud Martel</name>
<affiliation wicri:level="3"><nlm:affiliation>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Université du Maine , IMMM, UMR 6283 CNRS, 72085 Le Mans</wicri:regionArea>
<placeName><region type="region" nuts="2">Pays de la Loire</region>
<settlement type="city">Le Mans</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<affiliation wicri:level="3"><nlm:affiliation>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>Normandie Université , UNIHAVRE, URCOM, 76600 Le Havre 25, Rue Philipe Lebon, BP 540, F-76600 Le Havre</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
</affiliation>
</author>
</analytic>
<series><title level="j">Organic letters</title>
<idno type="eISSN">1523-7052</idno>
<imprint><date when="2016" type="published">2016</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">An original and rapid domino reaction for access to oxazolidin-4-ones is presented. Simply by heating α-bromoamido alcohol in the presence of KNaCO3 and water with readily prepared Michael acceptors, an unprecedented molecular rearrangement is generated. This new methodology enables the hitherto unreported synthesis of functionalized oxazolidin-4-ones. The process was proved to be compatible with a wide variety of substrates, and high regioselectivities were achieved.</div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Haute-Normandie</li>
<li>Pays de la Loire</li>
<li>Région Normandie</li>
</region>
<settlement><li>Le Havre</li>
<li>Le Mans</li>
</settlement>
</list>
<tree><country name="France"><region name="Région Normandie"><name sortKey="El Bouakher, Abderrahman" sort="El Bouakher, Abderrahman" uniqKey="El Bouakher A" first="Abderrahman" last="El Bouakher">Abderrahman El Bouakher</name>
</region>
<name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<name sortKey="Le Goff, Ronan" sort="Le Goff, Ronan" uniqKey="Le Goff R" first="Ronan" last="Le Goff">Ronan Le Goff</name>
<name sortKey="Lhoste, Jerome" sort="Lhoste, Jerome" uniqKey="Lhoste J" first="Jérôme" last="Lhoste">Jérôme Lhoste</name>
<name sortKey="Martel, Arnaud" sort="Martel, Arnaud" uniqKey="Martel A" first="Arnaud" last="Martel">Arnaud Martel</name>
<name sortKey="Tasserie, Jordan" sort="Tasserie, Jordan" uniqKey="Tasserie J" first="Jordan" last="Tasserie">Jordan Tasserie</name>
</country>
</tree>
</affiliations>
</record>

Pour manipuler ce document sous Unix (Dilib)

EXPLOR_STEP=$WICRI_ROOT/Wicri/France/explor/LeHavreV1/Data/Main/Exploration

HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000036 | SxmlIndent | more

HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000036 | SxmlIndent | more

Pour mettre un lien sur cette page dans le réseau Wicri

{{Explor lien
   |wiki=    Wicri/France
   |area=    LeHavreV1
   |flux=    Main
   |étape=   Exploration
   |type=    RBID
   |clé=     pubmed:27128809
   |texte=   Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.
}}

Pour générer des pages wiki

HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i   -Sk "pubmed:27128809" \
       | HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd   \
       | NlmPubMed2Wicri -a LeHavreV1

This area was generated with Dilib version V0.6.25.
Data generation: Sat Dec 3 14:37:02 2016. Site generation: Tue Mar 5 08:25:07 2024

Serveur d'exploration sur la visibilité du Havre

Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.

Synthesis of Oxazolidin-4-ones: Domino O-Alkylation/Aza-Michael/Intramolecular Retro-Claisen Condensation.

Source :

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki

	Serveur d'exploration sur la visibilité du Havre
	Attention, ce site est en cours de développement ! Attention, site généré par des moyens informatiques à partir de corpus bruts. Les informations ne sont donc pas validées.