127075 20241125101142.0 doi 10.1002/adsc.202300393 sideral 134485 ART-2023-134485 eng Ardevines, Sandra Universidad de Zaragoza (orcid)0000-0002-0904-9180 Enantioselective C-P Bond Formation through C(sp3)-H Functionalization 2023 Access copy available to the general public Unrestricted An 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. info:eu-repo/grantAgreement/ES/DGA/E07-23R info:eu-repo/grantAgreement/ES/MCIN/AEI/PID2020-117455GB-I00 info:eu-repo/grantAgreement/ES/MICINN/PID2019-104379RB-C21 info:eu-repo/semantics/openAccess by-nc-nd http://creativecommons.org/licenses/by-nc-nd/3.0/es/ 4.4 2023 CHEMISTRY, ORGANIC 8 / 58 = 0.138 2023 Q1 T1 CHEMISTRY, APPLIED 19 / 74 = 0.257 2023 Q2 T1 1.02 2023 Organic Chemistry 2023 Q1 Catalysis 2023 Q2 9.4 2023 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Horn, Devan Alegre-Requena, Juan V. (orcid)0000-0002-0769-7168 González-Jiménez, Marta Gimeno, M. Concepción (orcid)0000-0003-0553-0695 Marqués-López, Eugenia Universidad de Zaragoza (orcid)0000-0001-6832-8983 Herrera, Raquel P. (orcid)0000-0002-5244-9569 2013 765 Universidad de Zaragoza Dpto. Química Orgánica Área Química Orgánica 365, 13 (2023), 2152-2158 Adv. synth. catal. Advanced Synthesis and Catalysis 1615-4150 6440002 http://zaguan.unizar.es/record/127075/files/texto_completo.pdf Versión publicada 2810892 http://zaguan.unizar.es/record/127075/files/texto_completo.jpg?subformat=icon icon Versión publicada oai:zaguan.unizar.es:127075 articulos driver 2024-11-22-12:02:59 ARTICLE