Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked indoles.
Identifieur interne : 000850 ( Main/Exploration ); précédent : 000849; suivant : 000851Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked indoles.
Auteurs : RBID : pubmed:23738835English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Alcohols, Ketones.
- chemical , chemistry : Alcohols, Gold, Indoles, Ketones, Palladium.
- Catalysis, Cyclization, Molecular Structure.
Abstract
The preparation of previously unknown (indol-3-yl)-α-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium-mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal-catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N-(2-pyridyl)sulfonyl group. For allenols, gold-catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while 5-endo carbocyclization adducts were the major components starting from N-SO2py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.
DOI: 10.1021/jo401013d
PubMed: 23738835
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked indoles.</title><author><name sortKey="Alcaide, Benito" uniqKey="Alcaide B">Benito Alcaide</name><affiliation wicri:level="1"><nlm:affiliation>Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid</wicri:regionArea></affiliation></author><author><name sortKey="Almendros, Pedro" uniqKey="Almendros P">Pedro Almendros</name></author><author><name sortKey="Alonso, Jose M" uniqKey="Alonso J">José M Alonso</name></author><author><name sortKey="Fern Ndez, Israel" uniqKey="Fern Ndez I">Israel Fernández</name></author></titleStmt><publicationStmt><date when="2013">2013</date><idno type="doi">10.1021/jo401013d</idno><idno type="RBID">pubmed:23738835</idno><idno type="pmid">23738835</idno><idno type="wicri:Area/Main/Corpus">000595</idno><idno type="wicri:Area/Main/Curation">000595</idno><idno type="wicri:Area/Main/Exploration">000850</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alcohols (chemical synthesis)</term><term>Alcohols (chemistry)</term><term>Catalysis</term><term>Cyclization</term><term>Gold (chemistry)</term><term>Indoles (chemistry)</term><term>Ketones (chemical synthesis)</term><term>Ketones (chemistry)</term><term>Molecular Structure</term><term>Palladium (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Alcohols</term><term>Ketones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alcohols</term><term>Gold</term><term>Indoles</term><term>Ketones</term><term>Palladium</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Cyclization</term><term>Molecular Structure</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The preparation of previously unknown (indol-3-yl)-α-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium-mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal-catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N-(2-pyridyl)sulfonyl group. For allenols, gold-catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while 5-endo carbocyclization adducts were the major components starting from N-SO2py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">23738835</PMID><DateCreated><Year>2013</Year><Month>07</Month><Day>05</Day></DateCreated><DateCompleted><Year>2014</Year><Month>01</Month><Day>28</Day></DateCompleted><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>78</Volume><Issue>13</Issue><PubDate><Year>2013</Year><Month>Jul</Month><Day>5</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Carbocyclization versus oxycyclization on the metal-catalyzed reactions of oxyallenyl C3-linked indoles.</ArticleTitle><Pagination><MedlinePgn>6688-701</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo401013d</ELocationID><Abstract><AbstractText>The preparation of previously unknown (indol-3-yl)-α-allenols and -allenones was accomplished from indole-3-carbaldehydes, through indium-mediated Barbier allenylation reaction taking advantage of the N-(2-pyridyl)sulfonyl group. Metal-catalyzed cyclizations of oxyallenyl C3-linked indoles proceeded in two ways depending on the presence or absence of the N-(2-pyridyl)sulfonyl group. For allenols, gold-catalyzed oxycyclization occurred in the presence of the protecting group; in the absence of the protecting group, palladium- and gold-catalyzed benzannulations operated. On the contrary, under gold catalysis furyl-indoles were obtained as exclusive products from NH-allenones, while 5-endo carbocyclization adducts were the major components starting from N-SO2py-protected allenones. These cyclization reactions have been developed experimentally, and their mechanisms have additionally been investigated by a computational study.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Alcaide</LastName><ForeName>Benito</ForeName><Initials>B</Initials><Affiliation>Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es</Affiliation></Author><Author ValidYN="Y"><LastName>Almendros</LastName><ForeName>Pedro</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Alonso</LastName><ForeName>José M</ForeName><Initials>JM</Initials></Author><Author ValidYN="Y"><LastName>Fernández</LastName><ForeName>Israel</ForeName><Initials>I</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2013</Year><Month>06</Month><Day>18</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Alcohols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Indoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Ketones</NameOfSubstance></Chemical><Chemical><RegistryNumber>5TWQ1V240M</RegistryNumber><NameOfSubstance>Palladium</NameOfSubstance></Chemical><Chemical><RegistryNumber>7440-57-5</RegistryNumber><NameOfSubstance>Gold</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Alcohols</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Cyclization</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Gold</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indoles</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Ketones</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Palladium</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2013</Year><Month>6</Month><Day>18</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2013</Year><Month>6</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2013</Year><Month>6</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>1</Month><Day>29</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo401013d</ArticleId><ArticleId IdType="pubmed">23738835</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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