000127075 001__ 127075
000127075 005__ 20241125101142.0
000127075 0247_ $$2doi$$a10.1002/adsc.202300393
000127075 0248_ $$2sideral$$a134485
000127075 037__ $$aART-2023-134485
000127075 041__ $$aeng
000127075 100__ $$0(orcid)0000-0002-0904-9180$$aArdevines, Sandra$$uUniversidad de Zaragoza
000127075 245__ $$aEnantioselective C-P Bond Formation through C(sp3)-H Functionalization
000127075 260__ $$c2023
000127075 5060_ $$aAccess copy available to the general public$$fUnrestricted
000127075 5203_ $$aAn enantioselective C−P bond formation has been developed through a C(sp3)−H activation in an oxidation step followed by an organocatalyzed hydrophosphonylation protocol. The asymmetric organocatalytic Pudovik reaction has been achieved following a one‐pot strategy, starting from different benzylic and allylic alcohols and dibenzyl phosphite, using MnO2 as the oxidant and a chiral squaramide as organocatalyst. The scope of the reaction provides enantiomerically enriched α‐hydroxy phosphonates with yields from 40% to >95% and enantioselectivities from 64% to >99%. Furthermore, the use of this methodology has been demonstrated to form a tetrasubstituted carbon stereocenter, generating an acetophenone derivative in situ, using diphenyl phosphite. Therefore, this approach represents an asymmetric strategy for constructing chiral C−P bonds, which are of interest to the pharmaceutical industry.
000127075 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E07-23R$$9info:eu-repo/grantAgreement/ES/MCIN/AEI/PID2020-117455GB-I00$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104379RB-C21
000127075 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc-nd$$uhttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
000127075 590__ $$a4.4$$b2023
000127075 592__ $$a1.02$$b2023
000127075 591__ $$aCHEMISTRY, ORGANIC$$b8 / 58 = 0.138$$c2023$$dQ1$$eT1
000127075 593__ $$aOrganic Chemistry$$c2023$$dQ1
000127075 591__ $$aCHEMISTRY, APPLIED$$b19 / 74 = 0.257$$c2023$$dQ2$$eT1
000127075 593__ $$aCatalysis$$c2023$$dQ2
000127075 594__ $$a9.4$$b2023
000127075 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000127075 700__ $$aHorn, Devan
000127075 700__ $$0(orcid)0000-0002-0769-7168$$aAlegre-Requena, Juan V.
000127075 700__ $$aGonzález-Jiménez, Marta
000127075 700__ $$0(orcid)0000-0003-0553-0695$$aGimeno, M. Concepción
000127075 700__ $$0(orcid)0000-0001-6832-8983$$aMarqués-López, Eugenia$$uUniversidad de Zaragoza
000127075 700__ $$0(orcid)0000-0002-5244-9569$$aHerrera, Raquel P.
000127075 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica
000127075 773__ $$g365, 13 (2023), 2152-2158$$pAdv. synth. catal.$$tAdvanced Synthesis and Catalysis$$x1615-4150
000127075 8564_ $$s6440002$$uhttps://zaguan.unizar.es/record/127075/files/texto_completo.pdf$$yVersión publicada
000127075 8564_ $$s2810892$$uhttps://zaguan.unizar.es/record/127075/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000127075 909CO $$ooai:zaguan.unizar.es:127075$$particulos$$pdriver
000127075 951__ $$a2024-11-22-12:02:59
000127075 980__ $$aARTICLE