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http://hdl.handle.net/2445/170414
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DC Field | Value | Language |
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dc.contributor.author | Teloxa, Saul F. | - |
dc.contributor.author | Kennington, Stuart C. D. | - |
dc.contributor.author | Camats Gangonells, Marc | - |
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 | 2020-09-09T11:18:22Z | - |
dc.date.available | 2021-04-08T05:10:23Z | - |
dc.date.issued | 2020-04-08 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/2445/170414 | - |
dc.description.abstract | A direct and highly enantioselective reaction of N-azidoacetyl-1,3-thiazolidine-2-thione with trimethyl orthoformate catalyzed by Tol-BINAPNiCl2 in the presence of TESOTf and 2,6-lutidine is reported. The heterocyclic scaffold can be easily removed by addition of a wide array of amines to give the corresponding enantiomerically pure 2-azido-3,3-dimethoxypropanamides in high yields. Appropriate manipulation of the N-benzyl amide derivative provides an efficient access to the antiepileptic agent lacosamide through a new enantioselective C−C bond-forming process. DFT computational studies uncover clues for the understanding of the remarkable stereocontrol of the addition of a nickel(II) enolate to a putative oxocarbenium intermediate from trimethyl orthoformate. | - |
dc.format.extent | 9 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Wiley-VCH | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1002/chem.202001057 | - |
dc.relation.ispartof | Chemistry-A European Journal, 2020, vol. 26, num. 49, p. 11540-11548 | - |
dc.relation.uri | https://doi.org/10.1002/chem.202001057 | - |
dc.rights | (c) Wiley-VCH, 2020 | - |
dc.source | Articles publicats en revistes (Química Inorgànica i Orgànica) | - |
dc.subject.classification | Anticonvulsius | - |
dc.subject.classification | Síntesi asimètrica | - |
dc.subject.classification | Compostos de níquel | - |
dc.subject.other | Anticonvulsants | - |
dc.subject.other | Asymmetric synthesis | - |
dc.subject.other | Nickel compounds | - |
dc.title | Direct, enantioselective, and nickel(II) catalyzed reactions of N-azidoacetyl thioimides with trimethyl orthoformate: a new combined methodology for the rapid synthesis of lacosamide and derivatives | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 702986 | - |
dc.date.updated | 2020-09-09T11:18:22Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
Files in This Item:
File | Description | Size | Format | |
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702986.pdf | 1.19 MB | Adobe PDF | View/Open |
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