000120908 001__ 120908
000120908 005__ 20240319081000.0
000120908 0247_ $$2doi$$a10.1002/ejoc.202101254
000120908 0248_ $$2sideral$$a126280
000120908 037__ $$aART-2022-126280
000120908 041__ $$aeng
000120908 100__ $$aSonsona, Isaac G.
000120908 245__ $$aInvestigation of squaramide catalysts in the Aldol reaction en route to Funapide
000120908 260__ $$c2022
000120908 5060_ $$aAccess copy available to the general public$$fUnrestricted
000120908 5203_ $$aFunapide is a 3, 3’-spirocyclic oxindole with promising analgesic activity. A reported pilot-plant scale synthesis of this chiral compound involves an asymmetric aldol reaction, catalyzed by a common bifunctional thiourea structure. In this work, we show that the swapping of the thiourea unit of the catalyst for a tailored squaramide group provides an equally active, but rewardingly more selective, catalyst for this aldol reaction (from 70.5 to 85 % ee). The reaction was studied first on a model oxindole compound. Then, the set of optimal conditions was applied to the target funapide intermediate. The applicability of these conditions seems limited to oxindoles bearing the 3-substituent of funapide. Exemplifying the characteristics of target-focused methodological development, this study highlights how a wide-range screening of catalysts and reaction conditions can provide non-negligible improvements in an industrially viable asymmetric transformation. © 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH
000120908 536__ $$9info:eu-repo/grantAgreement/ES/AEI/FEDER/CTQ2017-88091-P$$9info:eu-repo/grantAgreement/ES/AEI/PID2020-117455GB-I00$$9info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R
000120908 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000120908 590__ $$a2.8$$b2022
000120908 592__ $$a0.682$$b2022
000120908 591__ $$aCHEMISTRY, ORGANIC$$b16 / 52 = 0.308$$c2022$$dQ2$$eT1
000120908 593__ $$aPhysical and Theoretical Chemistry$$c2022$$dQ2
000120908 593__ $$aOrganic Chemistry$$c2022$$dQ2
000120908 594__ $$a5.5$$b2022
000120908 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000120908 700__ $$aVicenzi, Andrea
000120908 700__ $$aGuidotti, Marco
000120908 700__ $$aBisag, Giorgiana Denisa
000120908 700__ $$aFochi, Mariafrancesca
000120908 700__ $$0(orcid)0000-0002-5244-9569$$aPerez Herrera, Raquel
000120908 700__ $$aBernardi, Luca
000120908 773__ $$g11, 1 (2022), e202101254 [6 pp]$$pEUR J ORG CHEM$$tEuropean Journal of Organic Chemistry$$x1434-193X
000120908 8564_ $$s3625922$$uhttps://zaguan.unizar.es/record/120908/files/texto_completo.pdf$$yVersión publicada
000120908 8564_ $$s1605371$$uhttps://zaguan.unizar.es/record/120908/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000120908 909CO $$ooai:zaguan.unizar.es:120908$$particulos$$pdriver
000120908 951__ $$a2024-03-18-14:07:05
000120908 980__ $$aARTICLE