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Asymmetric diethyl- and diphenylzinc additions to aldehydes by using a fluorine-containing chiral amino alcohol: A striking temperature effect on the enantioselectivity, a minimal amino alcohol loading, and an efficient recycling of the amino alcohol

DC Field Value Language
dc.contributor.authorPark, Jin Kyoon-
dc.contributor.authorLee, Hong Geun-
dc.contributor.authorBolm, Carsten-
dc.contributor.authorKim, Byeong Moon-
dc.date.accessioned2024-04-22T05:15:10Z-
dc.date.available2024-04-22T05:15:10Z-
dc.date.created2024-04-22-
dc.date.created2024-04-22-
dc.date.created2024-04-22-
dc.date.created2024-04-22-
dc.date.created2024-04-22-
dc.date.issued2005-01-
dc.identifier.citationChemistry - A European Journal, Vol.11 No.3, pp.945-950-
dc.identifier.issn0947-6539-
dc.identifier.urihttps://hdl.handle.net/10371/199280-
dc.description.abstractA chiral pyrrolidinylmethanol derivative containing perfluoro-ponytails (5) was prepared from (S)-proline. The use of this perfluoro-substituted amino alcohol in catalytic asymmetric additions of organozinc reagents to aldehydes affords products with high enantioselectivities in both pure hexane and a mixture of hexane and FC-72 (perfluorohexane). Enantiomeric excesses up to 94 and 88 % ee have been achieved in Et2Zn and Ph2Zn additions, respectively. For the reactions in the biphasic solvent system, a striking temperature effect was observed. Thus, when the temperature was raised from 0 to 40 degreesC the ee value of the product increased from 81 to 92 %. Furthermore, the catalyst loading could be remarkably low, and with only 0.1 mol % of amino alcohol 5 a product with 90 % ee was obtained in the Et2Zn addition to benzaldehyde in hexane. The perfluoro-ligand was easily recovered by simple phase separation, and until the ninth repetition its reuse proceeded without significant loss of enantioselectivity and reactivity.-
dc.language영어-
dc.publisherJohn Wiley & Sons Ltd.-
dc.titleAsymmetric diethyl- and diphenylzinc additions to aldehydes by using a fluorine-containing chiral amino alcohol: A striking temperature effect on the enantioselectivity, a minimal amino alcohol loading, and an efficient recycling of the amino alcohol-
dc.typeArticle-
dc.identifier.doi10.1002/chem.200400703-
dc.citation.journaltitleChemistry - A European Journal-
dc.identifier.wosid000226714400016-
dc.identifier.scopusid2-s2.0-13244258362-
dc.citation.endpage950-
dc.citation.number3-
dc.citation.startpage945-
dc.citation.volume11-
dc.description.isOpenAccessN-
dc.contributor.affiliatedAuthorLee, Hong Geun-
dc.contributor.affiliatedAuthorKim, Byeong Moon-
dc.type.docTypeArticle-
dc.description.journalClass1-
dc.subject.keywordPlusPHENYL TRANSFER-
dc.subject.keywordPlusORGANOZINC REAGENTS-
dc.subject.keywordPlusAROMATIC-ALDEHYDES-
dc.subject.keywordPlusARYL TRANSFER-
dc.subject.keywordPlusCATALYSTS-
dc.subject.keywordPlusALKYLATION-
dc.subject.keywordPlusDIALKYLZINCS-
dc.subject.keywordPlusSYSTEM-
dc.subject.keywordPlusDERIVATIVES-
dc.subject.keywordPlusPROTONATION-
dc.subject.keywordAuthoramino alcohols-
dc.subject.keywordAuthorasymmetric catalysis-
dc.subject.keywordAuthorbiphasic catalysis-
dc.subject.keywordAuthorcatalyst recycling-
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