000120128 001__ 120128
000120128 005__ 20240319081025.0
000120128 0247_ $$2doi$$a10.1002/anie.202209159
000120128 0248_ $$2sideral$$a130855
000120128 037__ $$aART-2022-130855
000120128 041__ $$aeng
000120128 100__ $$aAscaso-Alegre, Christian
000120128 245__ $$aStereoselective three-step one-pot cascade combining Amino- and Biocatalysis to access Chiral y-Nitro Alcohols
000120128 260__ $$c2022
000120128 5060_ $$aAccess copy available to the general public$$fUnrestricted
000120128 5203_ $$ahe combination of small-molecule catalysis and enzyme catalysis represents an underexploited area of research with huge potential in asymmetric synthetic chemistry due to both compatibility of reaction conditions and complementary reactivity. Herein, we describe the telescopic synthesis of chiral nitro alcohols starting from commercially available benzaldehyde derivatives through the one-pot three-step chemoenzymatic cascade combination of a Wittig reaction, chiral-thiourea-catalysed asymmetric conjugate addition, and ketoreductase-mediated reduction to access the corresponding target compounds in moderate to excellent overall isolated yields (36–80 %) and high diastereomeric and enantiomeric ratios (up to >97 : 3). This represents the first example of the combination of an organocatalysed asymmetric conjugate addition via iminium ion activation and a bioreduction step catalysed by ketoreductases.
000120128 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E07-20R$$9info:eu-repo/grantAgreement/ES/MCIN/AEI/PID2020-117455GB-I00$$9info:eu-repo/grantAgreement/ES/MICINN/PID2020-113351RA-I00/AEI/10.13039/501100011033
000120128 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000120128 590__ $$a16.6$$b2022
000120128 592__ $$a5.573$$b2022
000120128 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b13 / 178 = 0.073$$c2022$$dQ1$$eT1
000120128 593__ $$aChemistry (miscellaneous)$$c2022$$dQ1
000120128 593__ $$aCatalysis$$c2022$$dQ1
000120128 594__ $$a26.3$$b2022
000120128 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000120128 700__ $$0(orcid)0000-0002-5244-9569$$aHerrera, Raquel P.
000120128 700__ $$0(orcid)0000-0002-3364-1512$$aMangas-Sánchez, Juan
000120128 773__ $$g61, 40 (2022), 5$$pAngew. Chem. (Int. ed.)$$tANGEWANDTE CHEMIE-INTERNATIONAL EDITION$$x1433-7851
000120128 8564_ $$s4340539$$uhttps://zaguan.unizar.es/record/120128/files/texto_completo.pdf$$yVersión publicada
000120128 8564_ $$s3394892$$uhttps://zaguan.unizar.es/record/120128/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000120128 909CO $$ooai:zaguan.unizar.es:120128$$particulos$$pdriver
000120128 951__ $$a2024-03-18-16:40:35
000120128 980__ $$aARTICLE