000075923 001__ 75923
000075923 005__ 20190709135648.0
000075923 0247_ $$2doi$$a10.1002/adsc.201700986
000075923 0248_ $$2sideral$$a104274
000075923 037__ $$aART-2017-104274
000075923 041__ $$aeng
000075923 100__ $$aJuste-Navarro, Verónica$$uUniversidad de Zaragoza
000075923 245__ $$aA case study of Thiourea-assisted Iminium formation by hydroxyl anion binding: kinetic, spectroscopic and computational evidences
000075923 260__ $$c2017
000075923 5060_ $$aAccess copy available to the general public$$fUnrestricted
000075923 5203_ $$aThe experimental and computational study of the mechanism of the iminium-organocatalyzed formation of N-hydroxypyrrolidines from nitrones, revealed up to three activation levels of the Schreiner''s thiourea used as co-catalyst, i.e: (i) formation of the iminium ion through hydroxyl anion recognition forming a stable ion pair; (ii) enolization of the nitrone through a H-bond network and (iii) activation of the nitrone moiety towards the final ring closure. The computational model supports the mechanism and the catalytic cycle. This mechanistic rationale is supported by the lack of reactivity of preformed iminium ion with the nitrone in the absence of thiourea-hydroxyl complex and the observed reactivity when a complex thiourea-tetrabutylammonium hydroxide is added. (Figure presented.).
000075923 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E10$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-52107-P$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R
000075923 540__ $$9info:eu-repo/semantics/openAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/
000075923 590__ $$a5.123$$b2017
000075923 591__ $$aCHEMISTRY, ORGANIC$$b7 / 57 = 0.123$$c2017$$dQ1$$eT1
000075923 591__ $$aCHEMISTRY, APPLIED$$b3 / 71 = 0.042$$c2017$$dQ1$$eT1
000075923 592__ $$a2.079$$b2017
000075923 593__ $$aOrganic Chemistry$$c2017$$dQ1
000075923 593__ $$aCatalysis$$c2017$$dQ1
000075923 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion
000075923 700__ $$aPrieto, Lither
000075923 700__ $$0(orcid)0000-0001-8355-2289$$aDelso, Ignacio$$uUniversidad de Zaragoza
000075923 700__ $$aManzano, Rubén
000075923 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, Tomás$$uUniversidad de Zaragoza
000075923 700__ $$aReyes, Efraim
000075923 700__ $$aVicario, José L.
000075923 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, Pedro$$uUniversidad de Zaragoza
000075923 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000075923 773__ $$g359, 23 (2017), 4122-4128$$pAdv. synth. catal.$$tAdvanced Synthesis and Catalysis$$x1615-4150
000075923 8564_ $$s206163$$uhttps://zaguan.unizar.es/record/75923/files/texto_completo.pdf$$yPostprint
000075923 8564_ $$s124601$$uhttps://zaguan.unizar.es/record/75923/files/texto_completo.jpg?subformat=icon$$xicon$$yPostprint
000075923 909CO $$ooai:zaguan.unizar.es:75923$$particulos$$pdriver
000075923 951__ $$a2019-07-09-12:42:08
000075923 980__ $$aARTICLE