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http://hdl.handle.net/2445/165397
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DC Field | Value | Language |
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dc.contributor.author | Gómez-Palomino, A. | - |
dc.contributor.author | Pellicena Zanón, Miquel | - |
dc.contributor.author | Romo Fernández, Juan Manuel | - |
dc.contributor.author | Solà, R. | - |
dc.contributor.author | Romea, Pedro | - |
dc.contributor.author | Urpí Tubella, Fèlix | - |
dc.contributor.author | Font Bardia, Ma. Mercedes | - |
dc.date.accessioned | 2020-06-13T07:34:20Z | - |
dc.date.available | 2020-06-13T07:34:20Z | - |
dc.date.issued | 2014-08 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/2445/165397 | - |
dc.description.abstract | A highly efficient and straightforward aminoxylation of titanium(IV) enolates from (S)-N-acyl-4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-ones with TEMPO has been developed. A wide array of functional groups on the acyl moiety, including alkyl and aryl substituents, olefins, esters, or a-cyclopropyl, as well as a-trifluoromethyl groups, are well tolerated. This transformation can therefore produce the a-aminoxylated adducts in excellent yields with high diastereomeric ratios (d.r.). In turn, parallel additions to the a,b-unsaturated N-acyl counterparts give the corresponding g-adducts with complete regioselectivity in moderate to good yields. Removal of the piperidinyl moiety or the chiral auxiliary converts the resultant adducts into enantiomerically pure a-hydroxy carboxyl derivatives, alcohols, or esters in high yields under mild conditions. Finally, a new mechanistic model based on the biradical character of the titanium(IV) enolates has been proposed. | - |
dc.format.extent | 30 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.201402127 | - |
dc.relation.ispartof | Chemistry-A European Journal, 2014, vol. 20, num. 32, p. 10153-10159 | - |
dc.relation.uri | https://doi.org/10.1002/chem.201402127 | - |
dc.rights | (c) Wiley-VCH, 2014 | - |
dc.source | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) | - |
dc.subject.classification | Titani | - |
dc.subject.classification | Síntesi asimètrica | - |
dc.subject.other | Titanium | - |
dc.subject.other | Asymmetric synthesis | - |
dc.title | Stereoselective aminoxylation of biradical titanium enolates with TEMPO | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 641197 | - |
dc.date.updated | 2020-06-13T07:34:20Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada) |
Files in This Item:
File | Description | Size | Format | |
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641197.pdf | 1.53 MB | Adobe PDF | View/Open |
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