Regio- and stereoselective aminopentadienylation of carbonyl compounds.
Identifieur interne : 000063 ( Main/Exploration ); précédent : 000062; suivant : 000064Regio- and stereoselective aminopentadienylation of carbonyl compounds.
Auteurs : RBID : pubmed:24490803Abstract
A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration-oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group.
DOI: 10.1021/jo402854z
PubMed: 24490803
Links toward previous steps (curation, corpus...)
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Regio- and stereoselective aminopentadienylation of carbonyl compounds.</title><author><name sortKey="Bosque, Irene" uniqKey="Bosque I">Irene Bosque</name><affiliation wicri:level="1"><nlm:affiliation>Departamento de Quı́mica Orgánica, Facultad de Ciencias and Instituto de Sı́ntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Departamento de Quı́mica Orgánica, Facultad de Ciencias and Instituto de Sı́ntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante</wicri:regionArea></affiliation></author><author><name sortKey="Bagdatli, Emine" uniqKey="Bagdatli E">Emine Bagdatli</name></author><author><name sortKey="Foubelo, Francisco" uniqKey="Foubelo F">Francisco Foubelo</name></author><author><name sortKey="Gonzalez Gomez, Jose C" uniqKey="Gonzalez Gomez J">Jose C Gonzalez-Gomez</name></author></titleStmt><publicationStmt><date when="2014">2014</date><idno type="doi">10.1021/jo402854z</idno><idno type="RBID">pubmed:24490803</idno><idno type="pmid">24490803</idno><idno type="wicri:Area/Main/Corpus">000186</idno><idno type="wicri:Area/Main/Curation">000186</idno><idno type="wicri:Area/Main/Exploration">000063</idno></publicationStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration-oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="In-Process"><PMID Version="1">24490803</PMID><DateCreated><Year>2014</Year><Month>02</Month><Day>24</Day></DateCreated><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>79</Volume><Issue>4</Issue><PubDate><Year>2014</Year><Month>Feb</Month><Day>21</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Regio- and stereoselective aminopentadienylation of carbonyl compounds.</ArticleTitle><Pagination><MedlinePgn>1796-804</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo402854z</ELocationID><Abstract><AbstractText>A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration-oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Bosque</LastName><ForeName>Irene</ForeName><Initials>I</Initials><Affiliation>Departamento de Quı́mica Orgánica, Facultad de Ciencias and Instituto de Sı́ntesis Orgánica (ISO), Universidad de Alicante , Apdo. 99, 03080 Alicante, Spain.</Affiliation></Author><Author ValidYN="Y"><LastName>Bagdatli</LastName><ForeName>Emine</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Foubelo</LastName><ForeName>Francisco</ForeName><Initials>F</Initials></Author><Author ValidYN="Y"><LastName>Gonzalez-Gomez</LastName><ForeName>Jose C</ForeName><Initials>JC</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>02</Month><Day>06</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2014</Year><Month>2</Month><Day>6</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>2</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>2</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>2</Month><Day>5</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo402854z</ArticleId><ArticleId IdType="pubmed">24490803</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=IndiumV2/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000063 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000063 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= *** parameter Area/wikiCode missing ***
|area= IndiumV2
|flux= Main
|étape= Exploration
|type= RBID
|clé= pubmed:24490803
|texte= Regio- and stereoselective aminopentadienylation of carbonyl compounds.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:24490803" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a IndiumV2
| This area was generated with Dilib version V0.5.76. |  |