Asymmetric remote aldol cyclization reaction to synthesize trifluoromethylated heterospirocyclic frameworks

Trujillo-Sierra, José ; Sansano, José Miguel ; Pardos, Jorge (Universidad de Zaragoza) ; Tejero, Tomás (Universidad de Zaragoza) ; Merino, Pedro (Universidad de Zaragoza) ; Retamosa, María de Gracia

Resumen: The highly enantioselective organocatalytic synthesis of dihydropyran spirocyclic compounds bearing di- and trifluoromethyl groups by aldol cyclization reaction via trienamine using cyclic 2,5-dienones and different di- and trifluoromethylketones is described. Using a bifunctional aminothiourea catalyst, trifluoromethyl-functionalized dihydropyran spirocyclic products were obtained with good yields and enantioselectivities. Subsequent transformation with H2 and Pd/C has allowed the synthesis of the tetrahydropyran structure with three stereocenters. The plausible reaction mechanism was investigated by computational methods.

Idioma: Inglés

DOI: 10.1021/acs.joc.4c01839

Año: 2024

Publicado en: Journal of Organic Chemistry 89, 18 (2024), 13654-13660
ISSN: 0022-3263

Factor impacto JCR: 3.6 (2024)

Categ. JCR: CHEMISTRY, ORGANIC rank: 10 / 57 = 0.175 (2024) - Q1 - T1

Factor impacto CITESCORE: 6.1 - Organic Chemistry (Q2)

Factor impacto SCIMAGO: 0.737 - Organic Chemistry (Q2)

Financiación: info:eu-repo/grantAgreement/ES/AEI/RED2022-134331-T
Financiación: info:eu-repo/grantAgreement/ES/MICINN/RED2022-134287-T
Financiación: info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-82935-P
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/PID2019-107268GB-I00

Tipo y forma: Artículo (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)