Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines.
Identifieur interne : 000041 ( Main/Exploration ); précédent : 000040; suivant : 000042Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines.
Auteurs : RBID : pubmed:24447196Abstract
The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (-)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).
DOI: 10.1021/jo402759v
PubMed: 24447196
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines.</title><author><name sortKey="Sirvent, Juan Alberto" uniqKey="Sirvent J">Juan Alberto Sirvent</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante</wicri:regionArea></affiliation></author><author><name sortKey="Foubelo, Francisco" uniqKey="Foubelo F">Francisco Foubelo</name></author><author><name sortKey="Yus, Miguel" uniqKey="Yus M">Miguel Yus</name></author></titleStmt><publicationStmt><date when="2014">2014</date><idno type="doi">10.1021/jo402759v</idno><idno type="RBID">pubmed:24447196</idno><idno type="pmid">24447196</idno><idno type="wicri:Area/Main/Corpus">000202</idno><idno type="wicri:Area/Main/Curation">000202</idno><idno type="wicri:Area/Main/Exploration">000041</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (-)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).</div></front></TEI><pubmed><MedlineCitation Status="Publisher" Owner="NLM"><PMID Version="1">24447196</PMID><DateCreated><Year>2014</Year><Month>1</Month><Day>29</Day></DateCreated><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><PubDate><Year>2014</Year><Month>Jan</Month><Day>28</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Stereoselective Synthesis of Indoline, Tetrahydroquinoline, and Tetrahydrobenzazepine Derivatives from o-Bromophenyl N-tert-Butylsulfinyl Aldimines.</ArticleTitle><Pagination><MedlinePgn></MedlinePgn></Pagination><Abstract><AbstractText NlmCategory="UNLABELLED">The diastereoselective addition of an allylic indium intermediate to chiral o-bromophenyl sulfinyl imine 4 proceeded with good levels of diastereoselectivity. The resulting homoallylic amine derivatives were transformed into lactams 7 and 12, which upon copper-mediated intramolecular N-arylation led to the formation of benzo-fused 1-azabicyclo[j.k.0]alkanes 8 and 13. Benzo-fused 2-allyl-substituted heterocycles 14 could also be prepared by means of a palladium-catalyzed N-arylation of the corresponding free amines. The synthesis of the alkaloid (-)-angustureine was easily accomplished from (S)-2-allyltetrahydroquinoline (14b).</AbstractText></Abstract><AuthorList><Author><LastName>Sirvent</LastName><ForeName>Juan Alberto</ForeName><Initials>JA</Initials><Affiliation>Departamento de Química Orgánica, Facultad de Ciencias and Instituto de Síntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</Affiliation></Author><Author><LastName>Foubelo</LastName><ForeName>Francisco</ForeName><Initials>F</Initials></Author><Author><LastName>Yus</LastName><ForeName>Miguel</ForeName><Initials>M</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType>JOURNAL ARTICLE</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>1</Month><Day>28</Day></ArticleDate></Article><MedlineJournalInfo><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>1</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>1</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>1</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>aheadofprint</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo402759v</ArticleId><ArticleId IdType="pubmed">24447196</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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