000126341 001__ 126341
000126341 005__ 20241125101137.0
000126341 0247_ $$2doi$$a10.1002/anie.202302416
000126341 0248_ $$2sideral$$a133750
000126341 037__ $$aART-2023-133750
000126341 041__ $$aeng
000126341 100__ $$aGaray, Gorka
000126341 245__ $$aOrganocatalytic Enantioselective Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement
000126341 260__ $$c2023
000126341 5060_ $$aAccess copy available to the general public$$fUnrestricted
000126341 5203_ $$aWe have demonstrated that the catalytic and enantioselective vinylcyclopropane-cyclopentene rearrangement can be carried out on (vinylcyclopropyl)acetaldehydes through activation via enamine intermediates. The reaction makes use of racemic starting materials that, upon ring opening facilitated by the catalytic generation of a donor-acceptor cyclopropane, deliver an acyclic iminium ion/dienolate intermediate in which all stereochemical information has been deleted. The final cyclization step forms the rearrangement product, showing that chirality transfer from the catalyst to the final compound is highly effective and leads to the stereocontrolled formation of a variety of structurally different cyclopentenes.
000126341 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E34-20R$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104090RB-100$$9info:eu-repo/grantAgreement/ES/MICIU-FEDER/PID2020-118422GB-I00
000126341 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000126341 590__ $$a16.1$$b2023
000126341 592__ $$a5.3$$b2023
000126341 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b14 / 231 = 0.061$$c2023$$dQ1$$eT1
000126341 593__ $$aChemistry (miscellaneous)$$c2023$$dQ1
000126341 593__ $$aCatalysis$$c2023$$dQ1
000126341 594__ $$a26.6$$b2023
000126341 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000126341 700__ $$aHurtado, Josebe
000126341 700__ $$0(orcid)0000-0003-4249-6748$$aPedrón, Manuel$$uUniversidad de Zaragoza
000126341 700__ $$aGarcía, Lorena
000126341 700__ $$aReyes, Efraim
000126341 700__ $$aSánchez-Díez, Eduardo
000126341 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, Tomás$$uUniversidad de Zaragoza
000126341 700__ $$aCarrillo, Luisa
000126341 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, Pedro$$uUniversidad de Zaragoza
000126341 700__ $$aVicario, Jose L.
000126341 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000126341 773__ $$g62, 22 (2023), e202302416 [7 pp.]$$pAngew. Chem. (Int. ed.)$$tAngewandte Chemie (International ed.)$$x1433-7851
000126341 8564_ $$s4455001$$uhttps://zaguan.unizar.es/record/126341/files/texto_completo.pdf$$yVersión publicada
000126341 8564_ $$s2978845$$uhttps://zaguan.unizar.es/record/126341/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000126341 909CO $$ooai:zaguan.unizar.es:126341$$particulos$$pdriver
000126341 951__ $$a2024-11-22-12:01:15
000126341 980__ $$aARTICLE