Highly selective indium mediated allylation of unprotected pentosylamines.
Identifieur interne : 000D19 ( Main/Exploration ); précédent : 000D18; suivant : 000D20Highly selective indium mediated allylation of unprotected pentosylamines.
Auteurs : RBID : pubmed:22360647Abstract
A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.
DOI: 10.1021/ol3002656
PubMed: 22360647
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The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="PubMed-not-MEDLINE"><PMID Version="1">22360647</PMID><DateCreated><Year>2012</Year><Month>03</Month><Day>16</Day></DateCreated><DateCompleted><Year>2012</Year><Month>06</Month><Day>12</Day></DateCompleted><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1523-7052</ISSN><JournalIssue CitedMedium="Internet"><Volume>14</Volume><Issue>6</Issue><PubDate><Year>2012</Year><Month>Mar</Month><Day>16</Day></PubDate></JournalIssue><Title>Organic letters</Title><ISOAbbreviation>Org. Lett.</ISOAbbreviation></Journal><ArticleTitle>Highly selective indium mediated allylation of unprotected pentosylamines.</ArticleTitle><Pagination><MedlinePgn>1536-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/ol3002656</ELocationID><Abstract><AbstractText>A straightforward functionalization of D-pentoses is reported, which affords homoallylaminopolyols in two steps and uses ion exchange chromatography as the only purification operation. The key indium-mediated allylation is effected on unprotected glycosylamines and occurs with good to excellent syn stereoselection. Validation of the synthetic utility of the method was exemplified by a 3-step synthesis of an optically active 1,2,3,6-tetrahydropyridine from D-xylose.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Behr</LastName><ForeName>Jean-Bernard</ForeName><Initials>JB</Initials><Affiliation>Université de Reims Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, CNRS UMR 7312, UFR des Sciences Exactes et Naturelles, 51687 Reims Cedex 2, France. jb.behr@univ-reims.fr</Affiliation></Author><Author ValidYN="Y"><LastName>Hottin</LastName><ForeName>Audrey</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Ndoye</LastName><ForeName>Alpha</ForeName><Initials>A</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>02</Month><Day>24</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Org Lett</MedlineTA><NlmUniqueID>100890393</NlmUniqueID><ISSNLinking>1523-7052</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2012</Year><Month>2</Month><Day>24</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>2</Month><Day>25</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>3</Month><Day>1</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2012</Year><Month>3</Month><Day>1</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/ol3002656</ArticleId><ArticleId IdType="pubmed">22360647</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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