Synthesis of sterically constrained tricyclic pyrrolidinyl alcohol ligands for the enantioselective ethylation of aryl aldehydes: Assessment of the influence of ring strain and N-alkyl chain length on asymmetric induction

Basit Öğe Kaydı
dc.authorid37098938400
dc.authorid57197789938
dc.contributor.authorSahin E.
dc.contributor.authorKilic H.
dc.date.accessioned20.04.201910:49:12
dc.date.accessioned2019-04-20T21:44:48Z
dc.date.available20.04.201910:49:12
dc.date.available2019-04-20T21:44:48Z
dc.date.issued2011
dc.departmentBayburt Üniversitesien_US
dc.description.abstractA series of chiral sterically constrained tricyclic pyrrolidinyl alcohol ligands were synthesized from the appropriate amino acids, and a comparative study of the activity and selectivity of the ligands for the enantioselective ethylation of aromatic aldehydes was carried out. The results obtained were compared with those previously reported for related monocyclic analogues; it was found that the bicyclo[2.2.2]octane backbone fused to pyrrolidine and the groups attached to the carbinol centre, as well as the chain length of the ?-amino alcohol, had a marked effect on the enantioselectivity. The enantioselective addition of dialkylzincs to aryl aldehydes in the presence of ligands with diethyl substituents on the carbinol carbon afforded (R)-sec-alcohols in up to 99% enantiomeric excess (ee). © 2011 Elsevier Ltd. All rights reserved.en_US
dc.identifier.doi10.1016/j.tetasy.2011.01.002
dc.identifier.endpage282
dc.identifier.issn0957-4166
dc.identifier.issue3
dc.identifier.scopus2-s2.0-79953647865en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.startpage277
dc.identifier.urihttps://dx.doi.org/10.1016/j.tetasy.2011.01.002
dc.identifier.urihttps://hdl.handle.net/20.500.12403/944
dc.identifier.volume22
dc.identifier.wosWOS:000290074800005en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.relation.ispartofTetrahedron Asymmetryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1,1,3 triphenylpropan 1 ol
dc.subject2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 3 phenylpropan 1 ol
dc.subject2 methyl 1 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1 phenylpropan 2 ol
dc.subject2 methyl 3 (octahydro 2h 4,7 ethanoisoindol 2 yl) 4 phenylbutan 2 ol
dc.subject3 ethyl 2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1 phenylpentan 3 ol
dc.subjectaldehyde
dc.subjectamino acid
dc.subjectbicyclo[2.2.2]octane derivative
dc.subjectdiethylzinc
dc.subjectmethanol
dc.subjectpyrrolidine derivative
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectenantioselectivity
dc.subjectpriority journal
dc.subjectsynthesis
dc.subject2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1,1,3 triphenylpropan 1 ol
dc.subject2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 3 phenylpropan 1 ol
dc.subject2 methyl 1 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1 phenylpropan 2 ol
dc.subject2 methyl 3 (octahydro 2h 4,7 ethanoisoindol 2 yl) 4 phenylbutan 2 ol
dc.subject3 ethyl 2 (octahydro 2h 4,7 ethanoisoindol 2 yl) 1 phenylpentan 3 ol
dc.subjectaldehyde
dc.subjectamino acid
dc.subjectbicyclo[2.2.2]octane derivative
dc.subjectdiethylzinc
dc.subjectmethanol
dc.subjectpyrrolidine derivative
dc.subjectunclassified drug
dc.subjectarticle
dc.subjectenantioselectivity
dc.subjectpriority journal
dc.subjectsynthesis
dc.titleSynthesis of sterically constrained tricyclic pyrrolidinyl alcohol ligands for the enantioselective ethylation of aryl aldehydes: Assessment of the influence of ring strain and N-alkyl chain length on asymmetric inductionen_US
dc.typeArticleen_US

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