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http://hdl.handle.net/2445/191586
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DC Field | Value | Language |
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dc.contributor.author | Teloxa, Saul F. | - |
dc.contributor.author | Mellado Hidalgo, Miguel | - |
dc.contributor.author | Kennington, Stuart C. D. | - |
dc.contributor.author | Romea, Pedro | - |
dc.contributor.author | Urpí Tubella, Fèlix | - |
dc.contributor.author | Aullón López, Gabriel | - |
dc.contributor.author | Font Bardia, Ma. Mercedes | - |
dc.date.accessioned | 2022-12-14T16:49:00Z | - |
dc.date.available | 2022-12-14T16:49:00Z | - |
dc.date.issued | 2022-12-01 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/2445/191586 | - |
dc.description.abstract | A direct and asymmetric triisopropylsilyltrifluoromethanesulfonate (TIPSOTf) mediated aldol reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with aromatic aldehydes catalyzed by a chiral nickel(II)-Tol-BINAP complex has been developed (BINAP=2,2'-bis(diphenylphosphino)-1,1'-binaphthyl). The catalytic protocol gives the corresponding anti α-azido-β-silyloxy adducts with outstanding stereocontrol and in high yields. Theoretical calculations account for the stereochemical outcome of the reaction and lay the foundations for a mechanistic model. In turn, the easy removal of the thiazolidinethione yields a wide array of enantiomerically pure derivatives in a straightforward and efficient manner. Such a noteworthy character of the heterocyclic scaffold together with the appropriate manipulation of the azido group open a new route to the synthesis of di- and tripeptide blocks containing a β-aryl-β-hydroxy-α-amino acid. | - |
dc.format.extent | 10 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Wiley-VCH | - |
dc.relation.isformatof | Reproducció del document publicat a: https://doi.org/10.1002/chem.202200671 | - |
dc.relation.ispartof | Chemistry-A European Journal, 2022, vol. 28, num. 38, p. 1-10 | - |
dc.relation.uri | https://doi.org/10.1002/chem.202200671 | - |
dc.rights | cc-by-nc-nd (c) Teloxa, Saul F., et al, 2022 | - |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/es/ | * |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Síntesi asimètrica | - |
dc.subject.classification | Níquel | - |
dc.subject.classification | Reacció aldòlica | - |
dc.subject.other | Asymmetric synthesis | - |
dc.subject.other | Nickel | - |
dc.subject.other | Aldol reaction | - |
dc.title | Direct and Asymmetric Aldol Reactions of N-Azidoacetyl-1,3-thiazolidine-2-thione Catalyzed by Chiral Nickel(II) Complexes. A New Approach to the Synthesis of -Hydroxy--Amino Acids | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/publishedVersion | - |
dc.identifier.idgrec | 724127 | - |
dc.date.updated | 2022-12-14T16:49:01Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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724127.pdf | 4.94 MB | Adobe PDF | View/Open |
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