000075845 001__ 75845 000075845 005__ 20191127155458.0 000075845 0247_ $$2doi$$a10.1039/c7qo00858a 000075845 0248_ $$2sideral$$a105222 000075845 037__ $$aART-2018-105222 000075845 041__ $$aeng 000075845 100__ $$aMeazza, M. 000075845 245__ $$aSynergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight 000075845 260__ $$c2018 000075845 5060_ $$aAccess copy available to the general public$$fUnrestricted 000075845 5203_ $$aThe reaction of alkyl-benzoxazoles with enals has been reported using a synergistic approach. It consists of the activation of enals with a secondary amine catalyst and the activation of benzoxazoles with a metal Lewis acid. This approach has also been applied to the synthesis of cyclopropanes with excellent results. We demonstrated the applicability of this reaction in a cascade reaction (cyclopropanation + ring opening) that circumvents some of the limitations of the simple Michael addition between alkyl-benzoxazoles and enals. Finally, mechanistic studies have been reported to explain the stereoselectivity of the cyclopropanation reaction that renders an unusual cis conformation. 000075845 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E10$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R 000075845 540__ $$9info:eu-repo/semantics/openAccess$$aAll rights reserved$$uhttp://www.europeana.eu/rights/rr-f/ 000075845 590__ $$a5.076$$b2018 000075845 591__ $$aCHEMISTRY, ORGANIC$$b6 / 57 = 0.105$$c2018$$dQ1$$eT1 000075845 592__ $$a1.774$$b2018 000075845 593__ $$aOrganic Chemistry$$c2018$$dQ1 000075845 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion 000075845 700__ $$0(orcid)0000-0001-5823-7965$$aPolo, V.$$uUniversidad de Zaragoza 000075845 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza 000075845 700__ $$aRios, R. 000075845 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica 000075845 7102_ $$12012$$2755$$aUniversidad de Zaragoza$$bDpto. Química Física$$cÁrea Química Física 000075845 773__ $$g5, 5 (2018), 806-812$$pOrganic chemistry frontiers.$$tOrganic Chemistry Frontiers$$x2052-4129 000075845 8564_ $$s461848$$uhttps://zaguan.unizar.es/record/75845/files/texto_completo.pdf$$yPostprint 000075845 8564_ $$s99161$$uhttps://zaguan.unizar.es/record/75845/files/texto_completo.jpg?subformat=icon$$xicon$$yPostprint 000075845 909CO $$ooai:zaguan.unizar.es:75845$$particulos$$pdriver 000075845 951__ $$a2019-11-27-15:48:42 000075845 980__ $$aARTICLE