Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.
Identifieur interne : 000266 ( PubMed/Checkpoint ); précédent : 000265; suivant : 000267Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.
Auteurs : Frédéric Pin [France] ; Sébastien Comesse ; Bernard Garrigues ; Stefan Marchalín ; Adam DaïchSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2007.
Abstract
Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).
DOI: 10.1021/jo062077x
PubMed: 17243717
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
pubmed:17243717Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.</title>
<author><name sortKey="Pin, Frederic" sort="Pin, Frederic" uniqKey="Pin F" first="Frédéric" last="Pin">Frédéric Pin</name>
<affiliation wicri:level="4"><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP:540, F-76058 Le Havre Cedex, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP:540, F-76058 Le Havre Cedex</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>
<orgName type="university">Université du Havre</orgName>
</affiliation>
</author>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
</author>
<author><name sortKey="Garrigues, Bernard" sort="Garrigues, Bernard" uniqKey="Garrigues B" first="Bernard" last="Garrigues">Bernard Garrigues</name>
</author>
<author><name sortKey="Marchalin, Stefan" sort="Marchalin, Stefan" uniqKey="Marchalin S" first="Stefan" last="Marchalín">Stefan Marchalín</name>
</author>
<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2007">2007</date>
<idno type="RBID">pubmed:17243717</idno>
<idno type="pmid">17243717</idno>
<idno type="doi">10.1021/jo062077x</idno>
<idno type="wicri:Area/PubMed/Corpus">000278</idno>
<idno type="wicri:Area/PubMed/Curation">000278</idno>
<idno type="wicri:Area/PubMed/Checkpoint">000278</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.</title>
<author><name sortKey="Pin, Frederic" sort="Pin, Frederic" uniqKey="Pin F" first="Frédéric" last="Pin">Frédéric Pin</name>
<affiliation wicri:level="4"><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP:540, F-76058 Le Havre Cedex, France.</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP:540, F-76058 Le Havre Cedex</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>
<orgName type="university">Université du Havre</orgName>
</affiliation>
</author>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
</author>
<author><name sortKey="Garrigues, Bernard" sort="Garrigues, Bernard" uniqKey="Garrigues B" first="Bernard" last="Garrigues">Bernard Garrigues</name>
</author>
<author><name sortKey="Marchalin, Stefan" sort="Marchalin, Stefan" uniqKey="Marchalin S" first="Stefan" last="Marchalín">Stefan Marchalín</name>
</author>
<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
</author>
</analytic>
<series><title level="j">The Journal of organic chemistry</title>
<idno type="ISSN">0022-3263</idno>
<imprint><date when="2007" type="published">2007</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">17243717</PMID>
<DateCreated><Year>2007</Year>
<Month>2</Month>
<Day>9</Day>
</DateCreated>
<DateCompleted><Year>2007</Year>
<Month>04</Month>
<Day>17</Day>
</DateCompleted>
<DateRevised><Year>2007</Year>
<Month>2</Month>
<Day>9</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0022-3263</ISSN>
<JournalIssue CitedMedium="Print"><Volume>72</Volume>
<Issue>4</Issue>
<PubDate><Year>2007</Year>
<Month>Feb</Month>
<Day>16</Day>
</PubDate>
</JournalIssue>
<Title>The Journal of organic chemistry</Title>
<ISOAbbreviation>J. Org. Chem.</ISOAbbreviation>
</Journal>
<ArticleTitle>Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst.</ArticleTitle>
<Pagination><MedlinePgn>1181-91</MedlinePgn>
</Pagination>
<Abstract><AbstractText>Bismuth(III) triflate was found to promote the formation of stable cyclic N-acyliminium species in remarkable catalytic amounts (1 mol %). The alpha-amidoalkylation process seems to be effective in intermolecular and intramolecular manners leading to alpha-substituted lactams and heterocyclic systems containing azacycles, respectively. By comparing our results with those obtained with the classical Lewis acids as catalysts, it was evidenced clearly that the use of bismuth(III) triflate had been efficient for nearly all alpha-acetoxy lactams we used, except for N-acyliminium precursors bearing a sulfur atom. Also, the process seems to be easy, general, and clean, having diastereoselectivity comparable to protocols using classical Lewis acids and resulting in the formation of polyheterocyclic systems in good to excellent yields (64-99% in acetonitrile as solvent).</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Pin</LastName>
<ForeName>Frédéric</ForeName>
<Initials>F</Initials>
<AffiliationInfo><Affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP:540, F-76058 Le Havre Cedex, France.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Comesse</LastName>
<ForeName>Sébastien</ForeName>
<Initials>S</Initials>
</Author>
<Author ValidYN="Y"><LastName>Garrigues</LastName>
<ForeName>Bernard</ForeName>
<Initials>B</Initials>
</Author>
<Author ValidYN="Y"><LastName>Marchalín</LastName>
<ForeName>Stefan</ForeName>
<Initials>S</Initials>
</Author>
<Author ValidYN="Y"><LastName>Daïch</LastName>
<ForeName>Adam</ForeName>
<Initials>A</Initials>
</Author>
</AuthorList>
<Language>ENG</Language>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2007</Year>
<Month>Jan</Month>
<Day>23</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="pubmed"><Year>2007</Year>
<Month>1</Month>
<Day>25</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="medline"><Year>2007</Year>
<Month>1</Month>
<Day>25</Day>
<Hour>9</Hour>
<Minute>1</Minute>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2007</Year>
<Month>1</Month>
<Day>25</Day>
<Hour>9</Hour>
<Minute>0</Minute>
</PubMedPubDate>
</History>
<PublicationStatus>ppublish</PublicationStatus>
<ArticleIdList><ArticleId IdType="pubmed">17243717</ArticleId>
<ArticleId IdType="doi">10.1021/jo062077x</ArticleId>
</ArticleIdList>
</PubmedData>
</pubmed>
<affiliations><list><country><li>France</li>
</country>
<region><li>Haute-Normandie</li>
<li>Région Normandie</li>
</region>
<settlement><li>Le Havre</li>
</settlement>
<orgName><li>Université du Havre</li>
</orgName>
</list>
<tree><noCountry><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
<name sortKey="Garrigues, Bernard" sort="Garrigues, Bernard" uniqKey="Garrigues B" first="Bernard" last="Garrigues">Bernard Garrigues</name>
<name sortKey="Marchalin, Stefan" sort="Marchalin, Stefan" uniqKey="Marchalin S" first="Stefan" last="Marchalín">Stefan Marchalín</name>
</noCountry>
<country name="France"><region name="Région Normandie"><name sortKey="Pin, Frederic" sort="Pin, Frederic" uniqKey="Pin F" first="Frédéric" last="Pin">Frédéric Pin</name>
</region>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/France/explor/LeHavreV1/Data/PubMed/Checkpoint
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000266 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd -nk 000266 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Wicri/France |area= LeHavreV1 |flux= PubMed |étape= Checkpoint |type= RBID |clé= pubmed:17243717 |texte= Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/RBID.i -Sk "pubmed:17243717" \ | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd \ | NlmPubMed2Wicri -a LeHavreV1
![]() | This area was generated with Dilib version V0.6.25. | ![]() |