000061809 001__ 61809
000061809 005__ 20200221144254.0
000061809 0247_ $$2doi$$a10.1055/s-0035-1562500
000061809 0248_ $$2sideral$$a96305
000061809 037__ $$aART-2016-96305
000061809 041__ $$aeng
000061809 100__ $$aGarcía-Viñuales, S.
000061809 245__ $$aStereoselective Ethynylation and Propargylation of Chiral Cyclic Nitrones: Application to the Synthesis of Glycomimetics
000061809 260__ $$c2016
000061809 5060_ $$aAccess copy available to the general public$$fUnrestricted
000061809 5203_ $$aEthynylation and propargylation of chiral nonracemic polyhydroxylated cyclic nitrones with Grignard reagents are efficient methods for preparing building blocks containing an alkyne moiety to be used in copper-catalyzed azide alkyne cycloaddition click chemistry. Whereas ethynylation takes place with excellent diastereoselectivity, propargylation afforded mixtures of diastereomers in some cases. The use of (trimethylsilyl)propargyl bromide as precursor of the Grignard reagent is necessary to avoid the formation of undesired allene derivatives. DFT calculations explain, within the experimental error, the observed behavior. Cycloaddition of the obtained pyrrolidinyl alkynes with sugar azides derived from ß-(1, 3)-glucans provides glycomimetics suitable to be used against fungal transglycosylases.
000061809 536__ $$9info:eu-repo/grantAgreement/ES/MICINN/CTQ2013-44367-C2-1-P
000061809 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000061809 590__ $$a2.65$$b2016
000061809 591__ $$aCHEMISTRY, ORGANIC$$b22 / 59 = 0.373$$c2016$$dQ2$$eT2
000061809 592__ $$a1.066$$b2016
000061809 593__ $$aOrganic Chemistry$$c2016$$dQ1
000061809 593__ $$aCatalysis$$c2016$$dQ2
000061809 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/acceptedVersion
000061809 700__ $$0(orcid)0000-0001-8355-2289$$aDelso, I.$$uUniversidad de Zaragoza
000061809 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza
000061809 700__ $$0(orcid)0000-0003-3433-6701$$aTejero, T.$$uUniversidad de Zaragoza
000061809 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000061809 773__ $$g48, 19 (2016), 3339-3351$$pSynthesis (Stuttgart)$$tSYNTHESIS-STUTTGART$$x0039-7881
000061809 8564_ $$s376583$$uhttps://zaguan.unizar.es/record/61809/files/texto_completo.pdf$$yPostprint
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000061809 909CO $$ooai:zaguan.unizar.es:61809$$particulos$$pdriver
000061809 951__ $$a2020-02-21-13:29:24
000061809 980__ $$aARTICLE