Asymmetric Remote Aldol Cyclization Reaction to Synthesize Trifluoromethylated Heterospirocyclic Frameworks
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<sub>2</sub> and Pd/C has allowed the synthesis of the tetrahydropyran structure with three stereocenters. The plausible reaction mechanism was investigated by computational methods.
Authors
- José M. Sansano (ORCID: https://orcid.org/0000-0002-5536-2717)
- Pedro Merino (ORCID: https://orcid.org/0000-0002-2202-3460)
- J.J. Pardos
- María de Gracia Retamosa (ORCID: https://orcid.org/0000-0003-1131-5916)
- José Trujillo‐Sierra (ORCID: https://orcid.org/0000-0002-9294-5073)
- Tomás Tejero (ORCID: https://orcid.org/0000-0003-3433-6701)
Institutions
- University of Alicante (ES)
- Universidad de Zaragoza (ES)
- Instituto de Síntesis Química y Catálisis Homogénea (ES)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-09-05
- DOI
- https://doi.org/10.1021/acs.joc.4c01839
- Citations
- 8
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.66
Funders
- Universidad de Alicante
- Ministerio de Ciencia, Innovación y Universidades
- Ministerio de Economía y Competitividad
- Generalitat Valenciana