Asymmetric Remote Aldol Cyclization Reaction to Synthesize Trifluoromethylated Heterospirocyclic Frameworks
Year: 2024
Type: article
Abstract: 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 H 2 and Pd/C has allowed the synthesis of the tetrahydropyran structure with three stereocenters. The plausible reaction mechanism was investigated by computational methods.
Source: The Journal of Organic Chemistry
Authors: José Trujillo-Sierra, José Miguel Sansano, Jorge Pardos, Tomás Tejero, Pedro Merino, María de Gracia Retamosa
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4402273399