Use of tandem and domino processes for a fast access to N-heterocycles
Identifieur interne : 000367 ( Hal/Corpus ); précédent : 000366; suivant : 000368Use of tandem and domino processes for a fast access to N-heterocycles
Auteurs : Ronan Le GoffSource :
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Abstract
N-heterocycle scaffolds are found in many synthetic and medicinal chemical compounds explaining the high interest for developing efficient synthetic methodologies to reach such structures. In that field, our group has developed over the years innovative routes to y-lactams and bicyclic γ- and δ-lactams using tandem and domino reactions. Based on those previous works, we have developed two new methods to synthesize N-heterocycles. A tandem aza-MIRC (Michael Induced Ring Closure) sequence have been investigated to access pyrrolidines whereas the bicyclique scaffold of bislactames have been obtained using a domino oxa-Michael/aza-MIRC pathway. These two new methods have been then applied to the syntheses of more complexes and thus challenging backbones. The aza-MIRC tandem process have been used for the total and formal synthesis of alkaloids Coerulescine and Martinelline, respectively, whereas the domino oxa-Michael/aza-MIRC sequence has proved to be a powerful tool for stereoselective access to enantioenriched spirooxindolic compounds. DFT calculations studies have allowed elucidation of the diastereoselectivity and double chirality transfer of the domino reaction therefore could be used in the future to develop efficient total syntheses.
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In that field, our group has developed over the years innovative routes to y-lactams and bicyclic γ- and δ-lactams using tandem and domino reactions. Based on those previous works, we have developed two new methods to synthesize N-heterocycles. A tandem aza-MIRC (Michael Induced Ring Closure) sequence have been investigated to access pyrrolidines whereas the bicyclique scaffold of bislactames have been obtained using a domino oxa-Michael/aza-MIRC pathway. These two new methods have been then applied to the syntheses of more complexes and thus challenging backbones. The aza-MIRC tandem process have been used for the total and formal synthesis of alkaloids Coerulescine and Martinelline, respectively, whereas the domino oxa-Michael/aza-MIRC sequence has proved to be a powerful tool for stereoselective access to enantioenriched spirooxindolic compounds. DFT calculations studies have allowed elucidation of the diastereoselectivity and double chirality transfer of the domino reaction therefore could be used in the future to develop efficient total syntheses.</div></front></TEI><hal api="V3"><titleStmt><title xml:lang="en">Use of tandem and domino processes for a fast access to N-heterocycles</title><title xml:lang="fr">Utilisation de réactions tandem et domino pour l'accès rapide à des hétérocycles azotés</title><author role="aut"><persName><forename type="first">Ronan</forename><surname>Le Goff</surname></persName><email></email><idno type="halauthor">956037</idno><idno type="IdRef">http://www.idref.fr/19037599X</idno><affiliation ref="#struct-246592"></affiliation></author><editor role="depositor"><persName><forename>ABES</forename><surname>STAR</surname></persName><email>thelec@abes.fr</email></editor></titleStmt><editionStmt><edition n="v1" type="current"><date type="whenSubmitted">2016-04-02 01:02:47</date><date type="whenModified">2016-04-05 01:09:10</date><date type="whenReleased">2016-04-04 15:30:34</date><date type="whenProduced">2015-01-28</date><date type="whenEndEmbargoed">2016-04-02</date><ref type="file" target="https://tel.archives-ouvertes.fr/tel-01297048/document"><date notBefore="2016-04-02"></date></ref><ref type="file" subtype="author" n="1" target="https://tel.archives-ouvertes.fr/tel-01297048/file/Le_Goff_Ronan_2015.pdf"><date notBefore="2016-04-02"></date></ref></edition><respStmt><resp>contributor</resp><name key="131274"><persName><forename>ABES</forename><surname>STAR</surname></persName><email>thelec@abes.fr</email></name></respStmt></editionStmt><publicationStmt><distributor>CCSD</distributor><idno type="halId">tel-01297048</idno><idno type="halUri">https://tel.archives-ouvertes.fr/tel-01297048</idno><idno type="halBibtex">legoff:tel-01297048</idno><idno type="halRefHtml">Chimie organique. Université du Havre, 2015. Français. <NNT : 2015LEHA0014></idno><idno type="halRef">Chimie organique. Université du Havre, 2015. Français. <NNT : 2015LEHA0014></idno></publicationStmt><seriesStmt><idno type="stamp" n="STAR">STAR - Dépôt national des thèses électroniques</idno><idno type="stamp" n="UNIV-LEHAVRE">Université du Havre</idno><idno type="stamp" n="COMUE-NORMANDIE">Normandie Université</idno></seriesStmt><notesStmt></notesStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Use of tandem and domino processes for a fast access to N-heterocycles</title><title xml:lang="fr">Utilisation de réactions tandem et domino pour l'accès rapide à des hétérocycles azotés</title><author role="aut"><persName><forename type="first">Ronan</forename><surname>Le Goff</surname></persName><idno type="halAuthorId">956037</idno><idno type="IdRef">http://www.idref.fr/19037599X</idno><affiliation ref="#struct-246592"></affiliation></author></analytic><monogr><idno type="nnt">2015LEHA0014</idno><imprint><date type="dateDefended">2015-01-28</date></imprint><authority type="institution">Université du Havre</authority><authority type="school">École doctorale Normande de chimie (Caen)</authority><authority type="supervisor">Sébastien Comesse</authority><authority type="jury">Christophe Hoarau [Président]</authority><authority type="jury">Fabrice Denes [Rapporteur]</authority><authority type="jury">Thierry Constancieux [Rapporteur]</authority><authority type="jury">Arnaud Martel</authority><authority type="jury">Ata Martin Lawson</authority></monogr></biblStruct></sourceDesc><profileDesc><langUsage><language ident="fr">French</language></langUsage><textClass><keywords scheme="author"><term xml:lang="en">N-heterocycles</term><term xml:lang="en">Pyrrolidines</term><term xml:lang="en">Method development</term><term xml:lang="en">Y- and δ-lactams</term><term xml:lang="en">Tandem and domino process</term><term xml:lang="en">Total and formal synthesis</term><term xml:lang="en">Coerulescine</term><term xml:lang="en">Martinelline</term><term xml:lang="en">Spirooxindols</term><term xml:lang="fr">Hétérocycles azotés</term><term xml:lang="fr">Processus domino</term><term xml:lang="fr">Spirooxindoles</term><term xml:lang="fr">Pyrrolidones</term><term xml:lang="fr">Y- et δ-lactames</term></keywords><classCode scheme="halDomain" n="chim.orga">Chemical Sciences/Organic chemistry</classCode><classCode scheme="halTypology" n="THESE">Theses</classCode></textClass><abstract xml:lang="en">N-heterocycle scaffolds are found in many synthetic and medicinal chemical compounds explaining the high interest for developing efficient synthetic methodologies to reach such structures. In that field, our group has developed over the years innovative routes to y-lactams and bicyclic γ- and δ-lactams using tandem and domino reactions. Based on those previous works, we have developed two new methods to synthesize N-heterocycles. A tandem aza-MIRC (Michael Induced Ring Closure) sequence have been investigated to access pyrrolidines whereas the bicyclique scaffold of bislactames have been obtained using a domino oxa-Michael/aza-MIRC pathway. These two new methods have been then applied to the syntheses of more complexes and thus challenging backbones. The aza-MIRC tandem process have been used for the total and formal synthesis of alkaloids Coerulescine and Martinelline, respectively, whereas the domino oxa-Michael/aza-MIRC sequence has proved to be a powerful tool for stereoselective access to enantioenriched spirooxindolic compounds. DFT calculations studies have allowed elucidation of the diastereoselectivity and double chirality transfer of the domino reaction therefore could be used in the future to develop efficient total syntheses.</abstract><abstract xml:lang="fr">La présence importante des hétérocycles azotés en chimie organique et médicinale explique le grand intérêt et les très nombreuses recherches dont ils font l’objet. Parmi tous ces motifs, les pyrrolidines ainsi que les γ- et δ-lactames bicycliques ont tout particulièrement focalisé notre attention. En se basant sur des résultats antérieurs obtenus au laboratoire nous avons mis au point deux nouvelles voies d’accès rapides et innovantes pour accéder diastéréosélectivement à ces motifs. D’une part une réaction tandem aza-MIRC (Michael Induced Ring Closure) a permis de former des pyrrolidines polysubstituées et d’autre part une séquence domino oxa-Michael/aza-MIRC a donné accès à de très nombreux γ- et δ-lactames bicycliques. Ces deux méthodes ont, en outre, été appliquées à la synthèse de composés d’intérêts connus pour leurs activités biologiques. La séquence aza-MIRC a été utilisée pour les synthèses totale et formelle respectivement des alcaloïdes Coerulescine et Martinelline, tandis que le processus oxa-Michael/aza-MIRC a été employé pour accéder de manière stéréosélective à des composés spirooxindoliques énantioenrichis. En parallèle du développement de ces deux méthodes, une étude mécanistique poussée de la séquence oxa-Michael/aza-MIRC a été réalisée au moyen de calculs théoriques. Cette étude a permis d’expliquer la majeure partie des résultats obtenus en fournissant un outil puissant capable d’anticiper, dans une certaine mesure, la réactivité de la séquence domino oxa-Michael/aza-MIRC.</abstract></profileDesc></hal></record>Pour manipuler ce document sous Unix (Dilib)
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