Synthesis of chiral-at-metal rhodium complexes from achiral tripodal tetradentate ligands: resolution and application to enantioselective Diels–Alder and 1,3-dipolar cycloadditions
Tejero, Alvaro G. (Universidad de Zaragoza) ; Carmona, María ; Rodríguez, Ricardo ; Viguri, Fernando (Universidad de Zaragoza) ; Lahoz, Fernando J. ; García-Orduña, Pilar ; Carmona, Daniel
Resumen: An improved synthesis of the racemic rhodium compound [RhCl2(κ4C,N,N′,P-L1)] (1) containing an achiral tripodal tetradentate ligand is reported. Their derived solvate complexes [Rh(κ4C,N,N′,P-L1)(Solv)2][SbF6]2 (Solv = NCMe, 2; H2O, 3) are resolved into their two enantiomers. Complexes 2 and 3 catalyze the Diels–Alder (DA) reaction between methacrolein and cyclopentadiene and the 1,3-dipolar cycloaddition reaction between methacrolein and the nitrone N-benzylidenphenylamine-N-oxide. When enantiopure (ARh,RN)-2 was employed as the catalyst, enantiomeric ratios >99/1, in the R at C2 adduct, and up to 94/6, in the 3,5-endo isomer, were achieved in the DA reaction and in the 1,3-dipolar cycloaddition reaction, respectively. A plausible catalytic cycle that accounts for the origin of the observed enantioselectivity is proposed.
Idioma: Inglés
DOI: 10.1039/d2ra06982b
Año: 2022
Publicado en: RSC Advances 12, 53 (2022), 34704-34714
ISSN: 2046-2069
Factor impacto JCR: 3.9 (2022)
Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 74 / 178 = 0.416 (2022) - Q2 - T2
Factor impacto CITESCORE: 6.8 - Chemistry (Q1) - Chemical Engineering (Q2)
Factor impacto SCIMAGO: 0.678 - Chemistry (miscellaneous) (Q2) - Chemical Engineering (miscellaneous) (Q2)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E05-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-AEI-FEDER/PID2021-122406NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/CTQ2018-095561-BI00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes.
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Idioma: Inglés
DOI: 10.1039/d2ra06982b
Año: 2022
Publicado en: RSC Advances 12, 53 (2022), 34704-34714
ISSN: 2046-2069
Factor impacto JCR: 3.9 (2022)
Categ. JCR: CHEMISTRY, MULTIDISCIPLINARY rank: 74 / 178 = 0.416 (2022) - Q2 - T2
Factor impacto CITESCORE: 6.8 - Chemistry (Q1) - Chemical Engineering (Q2)
Factor impacto SCIMAGO: 0.678 - Chemistry (miscellaneous) (Q2) - Chemical Engineering (miscellaneous) (Q2)
Financiación: info:eu-repo/grantAgreement/ES/DGA/E05-20R
Financiación: info:eu-repo/grantAgreement/ES/MCIU-AEI-FEDER/PID2021-122406NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICINN/CTQ2018-095561-BI00
Tipo y forma: Article (Published version)
Área (Departamento): Área Química Inorgánica (Dpto. Química Inorgánica)
You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use. You may not use the material for commercial purposes. Exportado de SIDERAL (2025-02-10-08:31:19)
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Record created 2023-03-13, last modified 2025-02-10