000078979 001__ 78979
000078979 005__ 20200716101448.0
000078979 0247_ $$2doi$$a10.1039/C8SC05258A
000078979 0248_ $$2sideral$$a111456
000078979 037__ $$aART-2019-111456
000078979 041__ $$aeng
000078979 100__ $$aPutatunda, S.
000078979 245__ $$aProline bulky substituents consecutively act as steric hindrances and directing groups in a Michael/Conia-ene cascade reaction under synergistic catalysis
000078979 260__ $$c2019
000078979 5060_ $$aAccess copy available to the general public$$fUnrestricted
000078979 5203_ $$aIn this study, we report a highly stereoselective and versatile synthesis of spiro pyrazolones, promising motifs that are being employed as pharmacophores. The new synthetic strategy merges organocatalysis and metal catalysis to create a synergistic catalysis using proline derivatives and Pd catalysts. This protocol is suitable for late-stage functionalization, which is very important in drug discovery. Additionally, a thorough computational study proved to be very useful to elucidate the function of the different catalysts along the reaction, showing a peculiar feature: the-CPh 2 OSiMe 3 group of the proline catalyst switches its role during the reaction. In the initial Michael reaction, this group plays its commonly-assumed role of bulky blocking group, but the same group generates p-Pd interactions and acts as a directing group in the subsequent Pd-catalyzed Conia-ene reaction. This finding might be very relevant especially for processes with many steps, such as cascade reactions, in which functional groups are assumed to play the same role during all reaction steps.
000078979 536__ $$9info:eu-repo/grantAgreement/ES/DGA-FSE/E07-17R$$9info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-88091-P
000078979 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc$$uhttp://creativecommons.org/licenses/by-nc/3.0/es/
000078979 590__ $$a9.346$$b2019
000078979 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b21 / 177 = 0.119$$c2019$$dQ1$$eT1
000078979 592__ $$a3.756$$b2019
000078979 593__ $$aChemistry (miscellaneous)$$c2019$$dQ1
000078979 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000078979 700__ $$0(orcid)0000-0002-0769-7168$$aAlegre-Requena, J.V.
000078979 700__ $$aMeazza, M.
000078979 700__ $$aFranc, M.
000078979 700__ $$aRohal''ová, D.
000078979 700__ $$aVemuri, P.
000078979 700__ $$aCísarová, I.
000078979 700__ $$0(orcid)0000-0002-5244-9569$$aPérez Herrera, R.$$uUniversidad de Zaragoza
000078979 700__ $$aRios, R.
000078979 700__ $$aVeselý, J.
000078979 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000078979 773__ $$g10, 14 (2019), 4107-4115$$pChem. sci.$$tChemical Science$$x2041-6520
000078979 8564_ $$s612954$$uhttps://zaguan.unizar.es/record/78979/files/texto_completo.pdf$$yVersión publicada
000078979 8564_ $$s106296$$uhttps://zaguan.unizar.es/record/78979/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000078979 909CO $$ooai:zaguan.unizar.es:78979$$particulos$$pdriver
000078979 951__ $$a2020-07-16-09:04:40
000078979 980__ $$aARTICLE